Microbiocidal oxadiazole derivatives

ABSTRACT

Compounds of Formula (IA) or Formula (IB): (IA/IB) wherein the substituents are as defined in claim  1 , useful as pesticides, especially as fungicides.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a 371 National Stage application of InternationalApplication No. PCT/EP2017/062173, filed May 19, 2017, which claimspriority to European Patent Application No. 16170619.7 filed May 20,2016.

The present invention relates to microbiocidal oxadiazole derivatives,e.g., as active ingredients, which have microbiocidal activity, inparticular, fungicidal activity. The invention also relates toagrochemical compositions which comprise at least one of the oxadiazolederivatives, to processes of preparation of these compounds and to usesof the oxadiazole derivatives or compositions in agriculture orhorticulture for controlling or preventing infestation of plants,harvested food crops, seeds or non-living materials by phytopathogenicmicroorganisms, preferably fungi.

WO 2015/185485 describes the use of substituted oxadiazoles forcombating phytopathogenic fungi. Some phenyl oxadiazole derivatives arealso known from chemical libraries.

According to the present invention, there is provided a compound ofFormula (IA):

wherein

A¹ represents N or CR¹, wherein R¹ is hydrogen, halogen, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

A² represents N or CR², wherein R² is hydrogen, halogen, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

R³ and R⁴ independently represent hydrogen or halogen;

wherein when A¹ is CR¹ and A² is CR², 0 to 3 of R¹ to R⁴ are hydrogen;

n=0 or 1;

R⁵ and R⁶ independently represent hydrogen or methyl;

R⁷ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, C₃₋₆haloalkenyl, cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄haloalkoxyC₁₋₆alkyl,C₁₋₄alkylcarbonylC₁₋₄alkyl, C₁₋₄alkoxycarbonylC₁₋₄alkyl,C₁₋₄alkylaminocarbonylC₁₋₄alkyl, di-C₁₋₄alkylaminocarbonylC₁₋₄alkyl,C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl,heteroaryl, heteroarylC₁₋₃alkyl, wherein the heteroaryl moiety is a 5-or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₃alkyl or heterocyclyloxyC₁₋₃alkyl, wherein theheterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcomprises 1, 2 or 3 heteroatoms individually selected from N, O and S,and wherein any of cycloalkyl, phenyl, heteroaryl and heterocyclylmoieties are optionally substituted by 1, 2, 3 or 4 substituents, whichmay be the same or different, selected from R⁹;

R⁸ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,phenyl, or phenylC₁₋₃alkyl;

R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,C₁₋₄alkoxycarbonyl, C₁₋₄alkylaminocarbonyl, di-C₁₋₄alkylaminocarbonyl,or cyclopropyl; or

R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which theyare bonded, respectively, form (i) a 5- or 6-membered cycle optionallycontaining one additional heteroatom or group selected from O, S, N orNR¹⁰, wherein R¹⁰ is H or C₁₋₄alkyl, or (ii) a 7- to 11-memberednon-aromatic cyclic bridged ring system optionally containing oneadditional heteroatom or group selected from O, S, N or NR¹⁰, whereinR¹⁰ is H or C₁₋₄alkyl;

or a salt or an N-oxide thereof; or

a compound of Formula (IB):

wherein

A¹ is CR¹, wherein R¹ is hydrogen;

A² is CR², wherein R² is hydrogen;

R³ and R⁴ both represent hydrogen;

n=0 or 1;

R⁵ and R⁶ independently represent hydrogen or methyl;

R⁷ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, C₃₋₆haloalkenyl, cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄haloalkoxyC₁₋₆alkyl,C₁₋₄alkylcarbonylC₁₋₄alkyl, C₁₋₄alkoxycarbonylC₁₋₄alkyl,C₁₋₄alkylaminocarbonylC₁₋₄alkyl, di-C₁₋₄alkylaminocarbonylC₁₋₄alkyl,C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl,heteroaryl, heteroarylC₁₋₃alkyl, wherein the heteroaryl moiety is a 5-or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₃alkyl or heterocyclyloxyC₁₋₃alkyl wherein theheterocyclyl moiety is a 4- to 6-membered non-aromatic ring whichcomprises 1, 2 or 3 heteroatoms individually selected from N, O and S,and wherein any of said cycloalkyl, phenyl, heteroaryl and heterocyclylmoieties are optionally substituted by 1, 2, 3 or 4 substituents, whichmay be the same or different, selected from R⁹;

R⁸ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,phenyl, or phenylC₁₋₃alkyl;

R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,C₁₋₄alkoxycarbonyl, C₁₋₄alkylaminocarbonyl, di-C₁₋₄alkylaminocarbonyl,or cyclopropyl; or

R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which theyare bonded, respectively, form (i) a 5- or 6-membered cycle optionallycontaining one additional heteroatom or group selected from O, S, N orNR¹⁰, wherein R¹⁰ is H or C₁₋₄alkyl, or (ii) a 7- to 11-memberednon-aromatic cyclic bridged ring system optionally containing oneadditional heteroatom or group selected from O, S, N or NR¹⁰, whereinR¹⁰ is H or C₁₋₄alkyl;

or a salt or an N-oxide thereof;

with the proviso that the compound of Formula (IB) is not:

-   N-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide;-   N-methoxy-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide;-   N-benzyloxy-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide;    or-   N-methoxy-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide.

Surprisingly, it has been found that the novel compounds of Formula (IA)and (IB) have, for practical purposes, a very advantageous level ofbiological activity for protecting plants against diseases that arecaused by fungi.

According to a second aspect of the invention, there is provided anagrochemical composition comprising a fungicidally effective amount of acompound of Formula (IA) or (IB). Such an agricultural composition mayfurther comprise at least one additional active ingredient and/or anagrochemically-acceptable diluent or carrier.

According to a third aspect of the invention, there is provided a methodof controlling or preventing infestation of useful plants byphytopathogenic microorganisms, wherein a fungicidally effective amountof a compound of Formula (IA) or (IB), or a composition comprising thiscompound as active ingredient, is applied to the plants, to partsthereof or the locus thereof.

According to a fourth aspect of the invention, there is provided the useof a compound of Formula (IA) or (IB) as a fungicide. According to thisparticular aspect of the invention, the use may exclude methods for thetreatment of the human or animal body by surgery or therapy.

As used herein, the term “halogen” or “halo” refers to fluorine(fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo),preferably fluorine, chlorine or bromine.

As used herein, the term “C₁₋₆alkyl” refers to a straight or branchedhydrocarbon chain radical consisting solely of carbon and hydrogenatoms, containing no unsaturation, having from one to six carbon atoms,and which is attached to the rest of the molecule by a single bond.C₂₋₆alkyl, C₁₋₄alkyl, C₁₋₃alkyl and C₁₋₂alkyl are to be construedaccordingly. Examples of C₁₋₆alkyl include, but are not limited to,methyl, ethyl, n-propyl, 1-methylethyl (iso-propyl), n-butyl, and1-dimethylethyl (t-butyl). A “C₁₋₆alkylene” group refers to thecorresponding definition of C₁₋₆alkyl (and C₁₋₄alkyl and C₁₋₃alkyl),except that such radical is attached to the rest of the molecule by twosingle bonds. Examples of C₁₋₆alkylene, include, but are not limited to,—CH₂—, —CH₂CH₂— and —(CH₂)₃—.

As used herein, cyano means a —CN group.

As used herein, hydroxy means an —OH group.

As used herein, amino means an —NH₂ group.

As used herein, the term “C₁₋₆alkoxy” refers to a radical of the formula—OR_(a) where R_(a) is a C₁₋₆alkyl radical as generally defined above.C₁₋₄alkoxy and C₁₋₂alkoxy are to be construed accordingly. Examples ofC₁₋₆alkoxy include, but are not limited to, methoxy, ethoxy, propoxy,iso-propoxy, and t-butoxy.

As used herein, the term “C₁₋₄haloalkyl” refers to a C₁₋₄alkyl radicalas generally defined above substituted by one or more of the same ordifferent halogen atoms. The term C₁₋₂haloalkyl is to be construedaccordingly. Examples of C₁₋₄haloalkyl include, but are not limited tofluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl,2,2-difluoroethyl, and 2,2,2-trifluoroethyl.

As used herein, the term “C₃₋₆alkenyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one double bond that can be of either the(E)- or (Z)-configuration, having from three to six carbon atoms, whichis attached to the rest of the molecule by a single bond. C₃₋₄alkenyl isto be construed accordingly. Examples of C₃-C₆ alkenyl include, but arenot limited to, prop-1-enyl, allyl (prop-2-enyl), and but-1-enyl.

As used herein, the term “C₃₋₆alkynyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one triple bond, having from three to sixcarbon atoms, and which is attached to the rest of the molecule by asingle bond. The term “C₃₋₄alkynyl” is to be construed accordingly.Examples of C₃₋₆alkynyl include, but are not limited to, prop-1-ynyl,propargyl (prop-2-ynyl), and but-1-ynyl.

As used herein, the term “C₃₋₆haloalkenyl” refers to a C₃₋₆alkenyl groupas defined above substituted by one or more of the same or differenthalogen atoms. Examples of C₃₋₆haloalkenyl include, but are not limitedto 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichloroallyl,3,3-dibromoallyl, 2,3,3-tribromoallyl, and 2,3-dibromoallyl.

As used herein, the term “C₁₋₄haloalkoxy” refers to a C₁₋₄alkoxy groupas defined above substituted by one or more of the same or differenthalogen atoms. C₁₋₂haloalkoxy (including C₁₋₂fluoroalkoxy) is to beconstrued accordingly. Examples of C₁₋₄haloalkoxy include, but are notlimited to, fluoromethoxy, difluoromethoxy, fluoroethoxy,trifluoromethoxy, and trifluoroethoxy.

As used herein, the term “C₁₋₄alkoxyC₁₋₆alkyl” refers to radical of theformula R_(b)—O—R_(a)— where R_(b) is a C₁₋₄alkyl radical as generallydefined above, and R_(a) is a C₁₋₆alkylene radical as generally definedabove. C₁₋₄alkoxyC₁₋₄alkyl and C₁₋₂alkoxyC₁₋₄alkyl are to be construedaccordingly.

As used herein, the term “C₁₋₄haloalkoxyC₁₋₆alkyl” refers to radical ofthe formula R_(b)—O—R_(a)— where R_(b) is a C₁₋₄haloalkyl radical asgenerally defined above, and R_(a) is a C₁₋₆alkylene radical asgenerally defined above. C₁₋₂haloalkoxyC₁₋₄alkyl is to be construedaccordingly.

As used herein, the term “hydroxyC₁₋₆alkyl” refers to a C₁₋₆alkylradical as generally defined above substituted by one or more hydroxygroups. HydroxyC₁₋₄alkyl is to be construed accordingly.

As used herein, the term “cyanoC₁₋₆alkyl” refers to a C₁₋₆alkyl radicalas generally defined above substituted by one or more cyano groups.CyanoC₁₋₄alkyl is to be construed accordingly.

As used herein, the term “C₁₋₄alkylcarbonyl” refers to a radical of theformula —C(O)R_(a) where R_(a) is a C₁₋₄alkyl radical as generallydefined above.

As used herein, the term “C₁₋₆alkylcarbonylC₁₋₄alkyl” refers to aradical of the formula —R_(b)C(O)R_(a) where R_(a) is a C₁₋₆alkyl asgenerally defined above and R_(b) is a C₁₋₄alkylene radical as generallydefined above.

As used herein, the term “C₁₋₄alkoxycarbonyl” refers to a radical of theformula —C(O)OR_(a) where R_(a) is a C₁₋₄alkyl radical as generallydefined above.

As used herein, the term “C₁₋₄alkoxycarbonylC₁₋₄alkyl” refers to aradical of the formula —R_(b)C(O)OR_(a), where R_(a) is a C₁₋₄alkylradical as generally defined above and R_(b) is a C₁₋₄alkylene radicalas generally defined above.

As used herein, the term “C₁₋₄alkylaminocarbonyl” refers to a radical ofthe formula —C(O)NHR_(a) where R_(a) is a C₁₋₄alkyl radical as generallydefined above.

As used herein, the term “diC₁₋₄alkylaminocarbonyl” refers to a radicalof the formula —C(O)NR_(a)(R_(a)) where each R_(a) is independently aC₁₋₄alkyl radical as generally defined above.

As used herein, the term “C₁₋₄alkylaminocarbonylC₁₋₄alkyl” refers to aradical of the formula —R_(b)C(O)NHR_(a) where R_(a) is a C₁₋₄alkylradical as generally defined above and R_(b) is C₁₋₄alkylene radical asgenerally defined above.

As used herein, the term “C₃₋₈cycloalkyl” refers to a stable, monocyclicring radical which is saturated or partially unsaturated and contains 3to 8 carbon atoms. C₃₋₆cycloalkyl is to be construed accordingly.Examples of C₃₋₈cycloalkyl include, but are not limited to, cyclopropyl,cyclobutyl, cyclopentyl and cyclohexyl.

As used herein, the term “C₃₋₈cycloalkylC₁₋₃alkyl” refers to aC₃₋₈cycloalkyl ring as defined above attached to the rest of themolecule by a C₁₋₃alkylene radical as defined above. The terms“C₃₋₆cycloalkylC₁₋₃alkyl” and “C₃₋₄cycloalkylC₁₋₂alkyl” are to beconstrued accordingly. Examples of C₃₋₈cycloalkylC₁₋₃alkyl include, butare not limited to cyclopropyl-methyl, cyclobutyl-ethyl, andcyclopentyl-propyl.

As used herein, the term “phenylC₁₋₃alkyl” refers to a phenyl ringattached to the rest of the molecule by a C₁₋₃alkylene radical asdefined above. The term “phenylC₂₋₃alkyl” should be construedaccordingly. Examples of phenylC₁₋₃alkyl include, but are not limitedto, benzyl.

As used herein, the term “heteroaryl” refers to a 5- or 6-memberedmonocyclic aromatic ring radical which comprises 1, 2, 3 or 4heteroatoms individually selected from nitrogen, oxygen and sulfur. Theheteroaryl radical may be bonded to the rest of the molecule via acarbon atom or heteroatom. Examples of heteroaryl include, but are notlimited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl,thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl,pyrazinyl, pyridazinyl, pyrimidyl, pyridyl, and indolyl.

As used herein, the term “heteroarylC₁₋₃alkyl” refers to a heteroarylring as defined above which is attached to the rest of the molecule by aC₁₋₃alkylene radical as defined above.

As used herein, the term “heterocyclyl” or “heterocyclic” refers to astable 4-, 5- or 6-membered non-aromatic monocyclic ring radical or a 7-to 11-membered non-aromatic bridged ring system, which comprises 1, 2,or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur.The heterocyclyl radical may be bonded to the rest of the molecule via acarbon atom or heteroatom. Examples of heterocyclyl include, but are notlimited to, pyrrolinyl, pyrrolidyl, tetrahydrofuranyl,tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl, piperazinyl,tetrahydropyranyl, dioxolanyl, morpholinyl, δ-lactamyl,perhydroazepinyl, indolinyl, benzimidazole, oxetanyl, isoxazolidinyl,oxazinanyl, 3-oxa-2-azabicylo[2.2.2]octanyl, and3-oxa-2-azabicylo[2.2.2]octenyl. Preferably, examples of heterocyclylare piperidyl and tetrahydropyranyl.

As used herein, the term “heterocyclylC₁₋₃alkyl” refers to aheterocyclic ring as defined above which is attached to the rest of themolecule by a C₁₋₃alkylene radical as defined above.

As used herein, the term “heterocyclyloxyC₁₋₃alkyl” refers to aheterocyclic ring as defined above bound to an oxygen through a ringcarbon, wherein the oxygen is attached to the rest of the molecule by aC₁₋₃alkylene radical as defined above.

The presence of one or more possible asymmetric carbon atoms in acompound of Formula (IA) or (IB) means that the compounds may occur inchiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Alsoatropisomers may occur as a result of restricted rotation about a singlebond. Formulas (IA) and (IB) are intended to include all those possibleisomeric forms and mixtures thereof. The present invention includes allthose possible isomeric forms and mixtures thereof for compounds ofFormula (IA) and (IB). Likewise, Formulas (IA) and (IB) are intended toinclude all possible tautomers (including lactam-lactim tautomerism andketo-enol tautomerism) where present. The present invention includes allpossible tautomeric forms for a compound of Formula (I).

In each case, the compounds of Formula (IA) and (IB) according to theinvention are in free form, in oxidized form as an N-oxide, incovalently hydrated form, or in salt form, e.g., an agronomically usableor agrochemically acceptable salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms ofnitrogen containing heteroaromatic compounds. They are described forinstance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra,CRC Press, Boca Raton 1991.

Compounds of Formula (IB) which are not according to the presentinvention are:

Each of these aforementioned compounds not according to the inventionmay be used in a method of controlling or preventing infestation ofuseful plants by phytopathogenic microorganisms, wherein a fungicidallyeffective amount of the compound or a composition comprising thecompound as active ingredient is applied to the plants, to parts thereofor the locus thereof. Likewise, the aforementioned compounds notaccording to the invention may be useful as fungicidal agents.

The following list provides definitions, including preferreddefinitions, for substituents n, A¹, A², R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹ and R¹⁰, with reference to the compounds of Formula (IA) according tothe invention. For any one of these substituents, any of the definitionsgiven below may be combined with any definition of any other substituentgiven below or elsewhere in this document.

A¹ represents N or CR¹, wherein R¹ is hydrogen, halogen, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy.Preferably, A¹ represents N or CR¹, wherein R¹ is selected fromhydrogen, halogen or methyl. More preferably, R¹ is hydrogen, fluoro ormethyl. Most preferably, R¹ is hydrogen or fluoro.

A² represents N or CR², wherein R² is hydrogen, halogen, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy.Preferably, A² represents N or CR¹, wherein R¹ is selected fromhydrogen, halogen or methyl. More preferably, R² is hydrogen, fluoro ormethyl, and most preferably, hydrogen.

R³ represents hydrogen or halogen. Preferably, R³ is hydrogen or fluoro.

R⁴ represents hydrogen or halogen. Preferably, R⁴ is hydrogen or fluoro,and most preferably hydrogen.

In a further embodiment, R³ and R⁴ are both hydrogen.

When A¹ is CR¹ and A² is CR², 0, 1, 2, or 3 of R¹ to R⁴ are hydrogen.Preferably, when A¹ is CR¹ and A² is CR², 2 or 3 of R¹ to R⁴ arehydrogen. More preferably, when A¹ is CR¹ and A² is CR², 3 of R¹ to R⁴are hydrogen.

Preferably, A¹ is CR¹ and R¹ is halogen and preferably fluorine, A² isCR² and R² is hydrogen, and R³ and R⁴ are hydrogen; or A¹ is CR¹ and R¹is hydrogen, A² is CR² and R² is hydrogen; R³ is halogen and preferablyfluorine, and R⁴ is hydrogen.

In some embodiments, in the compounds of Formula (IA), A¹ is N, A² isCR² and R² is hydrogen, and R³ and R⁴ are hydrogen.

n represents 0 or 1. In some embodiments of the invention, n is 0. Inother embodiments of the invention, n is 1.

R⁵ and R⁶ independently represent hydrogen or methyl. Preferably, R⁵ andR⁶ are both hydrogen.

R⁷ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, C₃₋₆haloalkenyl, cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄haloalkoxyC₁₋₆alkyl,C₁₋₄alkylcarbonylC₁₋₄alkyl, C₁₋₄alkoxycarbonylC₁₋₄alkyl,C₁₋₄alkylaminocarbonylC₁₋₄alkyl, di-C₁₋₄alkylaminocarbonylC₁₋₄alkyl,C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl,heteroaryl, heteroarylC₁₋₃alkyl, wherein the heteroaryl moiety is a 5-or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₃alkyl or heterocyclyloxyC₁₋₃alkyl, wherein theheterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcomprises 1, 2 or 3 heteroatoms individually selected from N, O and S,and wherein any of cycloalkyl, phenyl, heteroaryl and heterocyclylmoieties are optionally substituted by 1, 2, 3 or 4 substituents, whichmay be the same or different, selected from R⁹.

Preferably, R⁷ is selected from hydrogen, C₁₋₆alkyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, hydroxyC₁₋₆alkyl, C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl, heteroaryl,heteroarylC₁₋₃alkyl, heterocyclyl, heterocyclylC₁₋₃alkyl, orheterocyclyloxyC₁₋₃alkyl, wherein any of said cycloalkyl, phenyl andheterocyclyl moieties are optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from R⁹.

More preferably, R⁷ is selected from hydrogen, C₁₋₄alkyl, C₃₋₄alkynyl,C₁₋₂haloalkyl, hydroxyC₁₋₄alkyl, C₃₋₆cycloalkyl,C₃₋₆cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl, furanyl,furanylC₁₋₃alkyl, piperidinyl, piperidinylC₁₋₃alkyl, ortetrahydropyranyloxyC₁₋₃alkyl, wherein any of said cycloalkyl, phenyl,furanyl, piperidinyl and tetrahydropyranyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁹.

Even more preferably, R⁷ is hydrogen, methyl, 2,2-difluoroethyl,(2,4,6-trichlorophenyl)methyl, 1-methyl-2-(2,4,6-trichlorophenyl)ethyl,benzyl, N-methoxy-4-methoxycarbonyl-piperidin-4-yl, furan-2-ylmethyl,cyclopropyl-methyl, 1-methyl-2-(tetrahydropyran-2-yloxy)ethyl,prop-2-ynyl, or 2-hydroxy-1-methyl-ethyl.

In some embodiments of the invention (Formula (IA)), R⁷ representsC₃₋₆alkenyl, C₃₋₆alkynyl, C₁₋₄haloalkyl, C₃₋₆haloalkenyl,cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,C₁₋₄haloalkoxyC₁₋₆alkyl, C₁₋₄alkylcarbonylC₁₋₄alkyl,C₁₋₄alkoxycarbonylC₁₋₄alkyl, C₁₋₄alkylaminocarbonylC₁₋₄alkyl,di-C₁₋₄alkylaminocarbonylC₁₋₄alkyl, C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl, heteroaryl,heteroarylC₁₋₃alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclyl, heterocyclylC₁₋₃alkyl orheterocyclyloxyC₁₋₃alkyl, wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of cycloalkyl,phenyl, heteroaryl and heterocyclyl moieties are optionally substitutedby 1, 2, 3 or 4 substituents, which may be the same or different,selected from R⁹. Preferably, R⁷ is selected from C₃₋₆alkynyl,hydroxyC₁₋₆alkyl, C₃₋₆cycloalkyl, C₃₋₆cycloalkylC₁₋₃alkyl, phenyl,phenylC₁₋₃alkyl, heteroaryl, heteroarylC₁₋₃alkyl, heterocyclyl,heterocyclylC₁₋₃alkyl, or heterocyclyloxyC₁₋₃alkyl, wherein any of saidcycloalkyl, phenyl and heterocyclyl moieties are optionally substitutedby 1, 2 or 3 substituents, which may be the same or different, selectedfrom R⁹.

When R⁷ comprises a cycloalkyl, phenyl, heteroaryl or heterocyclylmoiety, each cycloalkyl, phenyl, heteroaryl or heterocyclyl isoptionally substituted by 1, 2, 3 or 4 substituents, which may be thesame or different, selected from R⁹. Preferably, when R⁷ comprises acycloalkyl, phenyl, heteroaryl or heterocyclyl moiety, each cycloalkyl,phenyl, heteroaryl or heterocyclyl is optionally substituted by 1, 2 or3 substituents, which may be the same or different, selected from R⁹.More preferably, when R⁷ comprises a cycloalkyl, phenyl, heteroaryl orheterocyclyl moiety, each cycloalkyl, phenyl, heteroaryl or heterocyclylis optionally substituted by 1 or 2 substituents, which may be the sameor different, selected from R⁹. Even more preferably, when R⁷ comprisesa cycloalkyl, phenyl, heteroaryl or heterocyclyl moiety, eachcycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substitutedby a single substituent selected from R⁹.

R⁸ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,phenyl or phenylC₁₋₃alkyl. Preferably, hydrogen, C₁₋₄alkyl, C₃₋₆alkenyl,cyanoC₁₋₆alkyl, phenyl, or phenylC₁₋₃alkyl. More preferably, R⁸represents hydrogen, methyl, ethyl, prop-1-enyl, 1-methyl-2-cyano-ethylor benzyl. Most preferably, R⁸ is methyl.

In some embodiments of the invention, R⁸ represents hydrogen,C₃₋₆alkenyl, C₃₋₆alkynyl, C₁₋₄haloalkyl, cyanoC₁₋₆alkyl,hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl, phenyl or phenylC₁₋₃alkyl.Preferably, hydrogen, C₃₋₆alkenyl, cyanoC₁₋₆alkyl, phenyl, orphenylC₁₋₃alkyl. More preferably, R⁸ represents hydrogen, prop-1-enyl,1-methyl-2-cyano-ethyl or benzyl.

R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,C₁₋₄alkoxycarbonyl, C₁₋₄alkylaminocarbonyl, di-C₁₋₄alkylaminocarbonyl,or cyclopropyl. Preferably, R⁹ represents halogen, methoxy and C₁₋₄alkoxycarbonyl. More preferably, R⁹ represents chloro, methoxy andmethoxycarbonyl.

R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which theyare bonded, respectively, form (i) a 5- or 6-membered cycle optionallycontaining one additional heteroatom or group selected from O, S, N orNR¹⁰, wherein R¹⁰ is H or C₁₋₄alkyl, or (ii) a 7- to 11-memberednon-aromatic cyclic bridged ring system optionally containing oneadditional heteroatom or group selected from O, S, N or NR¹⁰, whereinR¹⁰ is H or C₁₋₄alkyl, in particular isoxazolidinyl, oxazinanyl,3-oxa-2-azabicyclo[2.2.2]octanyl, and3-oxa-2-azabicyclo[2.2.2]oct-5-enyl. Preferably, R⁷ and R⁸, togetherwith the nitrogen atom and oxygen atom to which they are bonded,respectively, form an isoxazolidinyl or oxazinanyl.

The following list provides definitions, including preferreddefinitions, for substituents n, A¹, A², R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹ and R¹⁰, with reference to the compounds of Formula (IB) according tothe invention. For any one of these substituents, any of the definitionsgiven below may be combined with any definition of any other substituentgiven below or elsewhere in this document.

A¹ is CR¹, wherein R¹ is hydrogen.

A² is CR², wherein R² is hydrogen.

R³ and R⁴ are both hydrogen.

n represents 0 or 1. In some embodiments of the invention, n is 0. Inother embodiments of the invention, n is 1.

R⁵ and R⁶ independently represent hydrogen or methyl. Preferably, R⁵ andR⁶ are each independently hydrogen.

R⁷ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, C₃₋₆haloalkenyl, cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄haloalkoxyC₁₋₆alkyl,C₁₋₄alkylcarbonylC₁₋₄alkyl, C₁₋₄alkoxycarbonylC₁₋₄alkyl,C₁₋₄alkylaminocarbonylC₁₋₄alkyl, di-C₁₋₄alkylaminocarbonylC₁₋₄alkyl,C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl,heteroaryl, heteroarylC₁₋₃alkyl, wherein the heteroaryl moiety is a 5-or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₃alkyl or heterocyclyloxyC₁₋₃alkyl wherein theheterocyclyl moiety is a 4- to 6-membered (preferably 5- or 6-membered),non-aromatic ring which comprises 1, 2 or 3 heteroatoms individuallyselected from N, O and S, and wherein any of said cycloalkyl, phenyl,heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2,3 or 4 substituents, which may be the same or different, selected fromR⁹.

Preferably, R⁷ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, C₃₋₆haloalkenyl, C₁₋₄alkoxycarbonylC₁₋₄alkyl,C₁₋₄alkylaminocarbonylC₁₋₄alkyl, phenyl, phenylC₁₋₃alkyl, heterocyclylor heterocyclylC₁₋₃alkyl, wherein any of said phenyl and heterocyclylmoieties are optionally substituted by 1, 2 or 3 substituents, which maybe the same or different, selected from R⁹.

More preferably, R⁷ represents hydrogen, C₁₋₄alkyl, C₃₋₄alkenyl,C₃₋₄alkynyl, C₁₋₄haloalkyl, C₃₋₄haloalkenyl,C₁₋₄alkoxycarbonylC₁₋₄alkyl, C₁₋₄alkylaminocarbonylC₁₋₄alkyl, phenyl,phenylC₁₋₃alkyl, piperidinyl or piperidinylC₁₋₃alkyl, wherein any ofsaid phenyl and piperidinyl moieties are optionally substituted by 1, 2or 3 substituents, which may be the same or different, selected from R⁹;

Even more preferably, R⁷ represents hydrogen, 2,2-difluoroethyl, benzyl,prop-2-enyl, prop-2-ynl, 3,3-dichloroprop-2-enyl,(methoxycarbonyl)methyl, (1-methoxycarbonyl)ethyl,N-methoxy-4-methoxycarbonyl-piperidin-4-yl,2-(tert-butylaminocarbonyl)ethyl, and 1-methyl-(2-methoxycarbonyl)ethyl.

In some embodiments of the invention (Formula (IB)), R⁷ representsC₂₋₄alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl, C₁₋₄haloalkyl, C₃₋₆haloalkenyl,cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,C₁₋₄haloalkoxyC₁₋₆alkyl, C₁₋₄alkylcarbonylC₁₋₄alkyl,C₁₋₄alkoxycarbonylC₁₋₄alkyl, C₁₋₄alkylaminocarbonylC₁₋₄alkyl,di-C₁₋₄alkylaminocarbonylC₁₋₄alkyl, C₃₋₆cycloalkyl,C₃₋₆cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl, heteroaryl,heteroarylC₁₋₃alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclyl, heterocyclylC₁₋₃alkyl orheterocyclyloxyC₁₋₃alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2, 3 or 4 substituents, which may be the same ordifferent, selected from R⁹. Preferably, R⁷ represents C₃₋₆alkenyl,C₃₋₆alkynyl, C₃₋₆haloalkenyl, C₁₋₄alkoxycarbonylC₁₋₄alkyl,C₁₋₄alkylaminocarbonylC₁₋₄alkyl, phenyl, phenylC₁₋₃alkyl, heterocyclylor heterocyclylC₁₋₃alkyl, wherein any of said phenyl and heterocyclylmoieties are optionally substituted by 1, 2 or 3 substituents, which maybe the same or different, selected from R⁹.

When R⁷ comprises a cycloalkyl, phenyl, heteroaryl or heterocyclylmoiety, each cycloalkyl, phenyl, heteroaryl or heterocyclyl isoptionally substituted by 1, 2, 3 or 4 substituents, which may be thesame or different, selected from R⁹. Preferably, when R⁷ comprises acycloalkyl, phenyl, heteroaryl or heterocyclyl moiety, each cycloalkyl,phenyl, heteroaryl or heterocyclyl is optionally substituted by 1, 2 or3 substituents, which may be the same or different, selected from R⁹.More preferably, when R⁷ comprises a cycloalkyl, phenyl, heteroaryl orheterocyclyl moiety, each cycloalkyl, phenyl, heteroaryl or heterocyclylis optionally substituted by 1 or 2 substituents, which may be the sameor different, selected from R⁹. Even more preferably, when R⁷ comprisesa cycloalkyl, phenyl, heteroaryl or heterocyclyl moiety, eachcycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substitutedby a single substituent selected from R⁹.

R⁸ represents hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,C₁₋₄haloalkyl, cyanoC₁₋₆alkyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,phenyl or phenylC₁₋₃alkyl. Preferably, R⁸ represents hydrogen,C₁₋₆alkyl, C₃₋₆alkenyl and C₃₋₆alkynyl. More preferably, R⁸ representshydrogen, methyl, ethyl, prop-1-ynyl, prop-1-enyl, or benzyl. Mostpreferably, R⁸ is methyl.

In some embodiments of the invention, R⁸ represents hydrogen,C₃₋₆alkenyl, C₃₋₆alkynyl, C₁₋₄haloalkyl, cyanoC₁₋₆alkyl,hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl, phenyl or phenylC₁₋₃alkyl.Preferably, R⁸ represents hydrogen, C₃₋₆alkenyl, cyanoC₁₋₆alkyl, phenyl,or phenylC₁₋₃alkyl. More preferably, R⁸ represents hydrogen,prop-1-enyl, 1-methyl-2-cyano-ethyl or benzyl.

R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,C₁₋₄alkoxycarbonyl, C₁₋₄alkylaminocarbonyl, di-C₁₋₄alkylaminocarbonyl,or cyclopropyl. Preferably, R⁹ is independently selected from methoxyand C₁₋₄alkoxycarbonyl. More preferably, R⁹ is independently selectedfrom methoxy and methoxycarbonyl.

R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which theyare bonded, respectively, form (i) a 5- or 6-membered cycle optionallycontaining one additional heteroatom or group selected from O, S, N orNR¹⁰, wherein R¹⁰ is H or C₁₋₄alkyl, or (ii) a 7- to 11-memberednon-aromatic cyclic bridged ring system optionally containing oneadditional heteroatom or group selected from O, S, N or NR¹⁰, whereinR¹⁰ is H or C₁₋₄alkyl, in particular isoxazolidinyl, oxazinanyl,3-oxa-2-azabicyclo[2.2.2]octanyl, and3-oxa-2-azabicyclo[2.2.2]oct-5-enyl. Preferably, R⁷ and R⁸, togetherwith the nitrogen atom and oxygen atom to which they are bonded,respectively, form an isoxazolidinyl or oxazinanyl.

Preferably, the compound according to Formula (IA) is selected from acompound 1.1 to 1.27 listed in Table T1 (below), and the compoundaccording to Formula (IB) is selected from a compound 2.1 to 2.26 listedin Table T2 (below).

Preferably, in a compound according to Formula (IA) of the invention, nis 0 or 1;

-   -   A¹ is CR¹ and R¹ is halogen and preferably fluorine, A² is CR²        and R² is hydrogen, and R³ and R⁴ are hydrogen; or A¹ is CR¹ and        R¹ is hydrogen, A² is CR² and R² is hydrogen; R³ is halogen and        preferably fluorine, and R⁴ is hydrogen;    -   R⁵ and R⁶ both represent hydrogen (when n is 1);    -   R⁷ is selected from hydrogen, C₁₋₆alkyl, C₃₋₆alkynyl,        C₁₋₄haloalkyl, hydroxyC₁₋₆alkyl, C₃₋₈cycloalkyl,        C₃₋₈cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl, heteroaryl,        heteroarylC₁₋₃alkyl, heterocyclyl, heterocyclylC₁₋₃alkyl, or        heterocyclyloxyC₁₋₃alkyl, wherein any of said cycloalkyl, phenyl        and heterocyclyl moieties are optionally substituted by 1, 2 or        3 substituents, which may be the same or different, selected        from R⁹;    -   R⁸ is selected from hydrogen, C₁₋₄alkyl, C₃₋₆alkenyl,        cyanoC₁₋₆alkyl, phenyl, or phenylC₁₋₃alkyl; and    -   R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl,        difluoromethyl, trifluoromethyl, methoxy, ethoxy,        difluoromethoxy, C₁₋₄alkoxycarbonyl, C₁₋₄alkylaminocarbonyl, or        di-C₁₋₄alkylaminocarbonyl;    -   or    -   R⁷ and R⁸, together with the nitrogen atom and oxygen atom to        which they are bonded, respectively, form (i) a 5- or 6-membered        cycle optionally containing one additional heteroatom or group        selected from O, S, N or NR¹⁰, wherein R¹⁰ is H or C₁₋₄alkyl,        or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring        system optionally containing one additional heteroatom or group        selected from O, S, N or NR¹⁰, wherein R¹⁰ is H or C₁₋₄alkyl.

More preferably, in a compound according to Formula (IA) of theinvention, n is 0.

-   -   A¹ is CR¹ and R¹ is halogen and preferably fluorine, A² is CR²        and R² is hydrogen, and R³ and R⁴ are hydrogen; or A¹ is CR¹ and        R¹ is hydrogen, A² is CR² and R² is hydrogen; R³ is halogen and        preferably fluorine, and R⁴ is hydrogen;    -   R⁷ is selected from hydrogen, C₁₋₄alkyl, C₃₋₄alkynyl,        C₁₋₄haloalkyl, hydroxyC₁₋₄alkyl, C₃₋₆cycloalkyl,        C₃₋₆cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl, furanyl,        furanylC₁₋₃alkyl, piperidinyl, piperidinylC₁₋₃alkyl, or        tetrahydropyranyloxyC₁₋₃alkyl wherein any of said cycloalkyl,        phenyl, furanyl, piperidinyl and tetrahydropyranyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R⁹;    -   R⁸ is selected from hydrogen, C₁₋₄alkyl, C₃₋₆alkenyl,        cyanoC₁₋₆alkyl, phenyl, or phenylC₁₋₃alkyl; and    -   R⁹ is selected from halogen, C₁₋₄alkoxy and C₁₋₄alkoxycarbonyl;    -   or    -   R⁷ and R⁸, together with the nitrogen atom and oxygen atom to        which they are bonded, respectively, form an isoxazolidinyl or        oxazinanyl.

Even more preferably, in a compound according to Formula (IA) of theinvention, n is 0.

-   -   A¹ is CR¹ and R¹ is halogen and preferably fluorine, A² is CR²        and R² is hydrogen, and R³ and R⁴ are hydrogen; or A¹ is CR¹ and        R¹ is hydrogen, A² is CR² and R² is hydrogen; R³ is halogen and        preferably fluorine, and R⁴ is hydrogen;    -   R⁷ is selected from hydrogen, C₁₋₄alkyl, C₁₋₂haloalkyl,        C₃₋₄alkynyl, hydroxyC₁₋₄alkyl, C₃₋₆cycloalkyl,        C₃₋₆cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl, furanyl,        furanylC₁₋₃alkyl, piperidinyl, piperidinylC₁₋₃alkyl, or        tetrahydropyranyloxyC₁₋₃alkyl wherein any of said cycloalkyl,        phenyl, furanyl, piperidinyl and tetrahydropyranyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R⁹;    -   R⁸ is selected from hydrogen or C₁₋₄alkyl (preferably, methyl);        and    -   R⁹ is selected from halogen, C₁₋₄alkoxy and C₁₋₄alkoxycarbonyl.

In some embodiments, in a compound according to Formula (IA) of theinvention, n is 0.

-   -   A¹ is CR¹ and R¹ is halogen and preferably fluorine, A² is CR²        and R² is hydrogen, and R³ and R⁴ are hydrogen; or A¹ is CR¹ and        R¹ is hydrogen, A² is CR² and R² is hydrogen; R³ is halogen and        preferably fluorine, and R⁴ is hydrogen;    -   R⁷ is selected from hydrogen, C₁₋₄alkyl, C₁₋₂haloalkyl,        C₃₋₄alkynyl, hydroxyC₁₋₄alkyl, C₃₋₆cycloalkyl,        C₃₋₆cycloalkylC₁₋₃alkyl, phenyl, phenylC₁₋₃alkyl, furanyl,        furanylC₁₋₃alkyl, piperidinyl, piperidinylC₁₋₃alkyl, or        tetrahydropyranyloxyC₁₋₃alkyl wherein any of said cycloalkyl,        phenyl, furanyl, piperidinyl and tetrahydropyranyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R⁹;    -   R⁸ is selected from hydrogen, C₃₋₆alkenyl, cyanoC₁₋₆alkyl,        phenyl, or phenylC₁₋₃alkyl; and    -   R⁹ is selected from halogen, C₁₋₄alkoxy and C₁₋₄alkoxycarbonyl.

Preferably, in a compound according to Formula (IB) of the invention, nis 0 or 1;

-   -   A¹ is CR¹, wherein R¹ is hydrogen;    -   A² is CR², wherein R² is hydrogen;    -   R³ and R⁴ both represent hydrogen;    -   R⁵ and R⁶ both represent hydrogen (when n is 1);    -   R⁷ is selected from hydrogen, C₁₋₆alkyl, C₁₋₄haloalkyl,        C₃₋₆alkenyl, C₃₋₆alkynyl, C₃₋₆haloalkenyl,        C₁₋₄alkoxycarbonylC₁₋₄alkyl, C₁₋₄alkylaminocarbonylC₁₋₄alkyl,        phenyl, phenylC₁₋₃alkyl, heterocyclyl or heterocyclylC₁₋₃alkyl,        wherein any of said phenyl and heterocyclyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R⁹;    -   R⁸ is selected from hydrogen, C₁₋₄alkyl, C₃₋₆alkenyl,        C₃₋₆alkynyl, phenyl or phenylC₁₋₃alkyl; and    -   R⁹ is selected from methoxy and methoxycarbonyl;    -   or    -   R⁷ and R⁸, together with the nitrogen atom and oxygen atom to        which they are bonded, respectively, form (i) a 5- or 6-membered        cycle optionally containing one additional heteroatom or group        selected from O, S, N or NR¹⁰, wherein R¹⁰ is H or C₁₋₄alkyl,        or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring        system optionally containing one additional heteroatom or group        selected from O, S, N or NR¹⁰, wherein R¹⁰ is H or C₁₋₄alkyl.

More preferably, in a compound according to Formula (IB) of theinvention, n is 0 or 1;

-   -   A¹ is CR¹, wherein R¹ is hydrogen;    -   A² is CR², wherein R² is hydrogen;    -   R³ and R⁴ both represent hydrogen;    -   R⁵ and R⁶ both represent hydrogen (when n is 1);    -   R⁷ is selected from hydrogen, C₁₋₄alkyl, C₁₋₂haloalkyl,        C₃₋₄alkenyl, C₃₋₄alkynyl, C₃₋₄haloalkenyl,        C₁₋₄alkoxycarbonylC₁₋₄alkyl, C₁₋₄alkylaminocarbonylC₁₋₄alkyl,        phenyl, phenylC₁₋₃alkyl, piperidinyl or piperidinylC₁₋₃alkyl        wherein any of said phenyl and piperidinyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R⁹;    -   R⁸ is selected from hydrogen, methyl, ethyl, prop-1-enyl,        prop-1-ynyl, and benzyl; and    -   R⁹ is selected from methoxy and methoxycarbonyl;    -   or    -   R⁷ and R⁸, together with the nitrogen atom and oxygen atom to        which they are bonded, respectively, form a        3-oxa-2-azabicyclo[2.2.2]octanyl or        3-oxa-2-azabicyclo[2.2.2]oct-5-enyl.

Even more preferably, in a compound according to Formula (IB) of theinvention, n is 0 or 1;

-   -   A¹ is CR¹, wherein R¹ is hydrogen;    -   A² is CR², wherein R² is hydrogen;    -   R³ and R⁴ both represent hydrogen;    -   R⁵ and R⁶ both represent hydrogen (when n is 1);    -   R⁷ is selected from hydrogen, C₁₋₄alkyl, C₃₋₄alkenyl,        C₃₋₄alkynyl, C₁₋₄haloalkyl, C₃₋₄haloalkenyl,        C₁₋₄alkoxycarbonylC₁₋₄alkyl, C₁₋₄alkylaminocarbonylC₁₋₄alkyl,        phenyl, phenylC₁₋₃alkyl, piperidinyl or piperidinylC₁₋₃alkyl        wherein any of said phenyl and piperidinyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R⁹;    -   R⁸ is selected from hydrogen, methyl or ethyl; and    -   R⁹ is selected from methoxy and methoxycarbonyl.

In some embodiments, in a compound according to Formula (IB) of theinvention, n is 0 or 1;

-   -   A¹ is CR¹, wherein R¹ is hydrogen;    -   A² is CR², wherein R² is hydrogen;    -   R³ and R⁴ both represent hydrogen;    -   R⁵ and R⁶ both represent hydrogen (when n is 1);    -   R⁷ is selected from hydrogen, C₁₋₄alkyl, C₃₋₄alkenyl,        C₃₋₄alkynyl, C₁₋₄haloalkyl, C₃₋₄haloalkenyl,        C₁₋₄alkoxycarbonylC₁₋₄alkyl, C₁₋₄alkylaminocarbonylC₁₋₄alkyl,        phenyl, phenylC₁₋₃alkyl, piperidinyl or piperidinylC₁₋₃alkyl        wherein any of said phenyl and piperidinyl moieties are        optionally substituted by 1, 2 or 3 substituents, which may be        the same or different, selected from R⁹;    -   R⁸ is selected from hydrogen, prop-1-enyl, prop-1-ynyl, and        benzyl; and    -   R⁹ is selected from methoxy and methoxycarbonyl.

The compounds of the present invention (when n=1) may be enantiomers ofthe compound of Formula (IA) as represented by a Formula (IA-a) or aFormula (IA-b) below, or the compound of Formula (IB) as represented bya Formula (IB-a) or a Formula (IB-b) below, and R⁵ and R⁶ are different.

It is understood that when in aqueous media, the compounds of Formula(IA) and Formula (IB) according to the invention may be present in areversible equilibrium with the corresponding covalently hydrated forms(e.g., as represented by the compounds of Formula (IA-I) and Formula(IA-III) or the compounds of Formula (IB-I) and Formula (IB-III), whichmay exist in tautomeric form as the compounds of Formula (IA-Ia) andFormula (IA-IIa) or Formula (IB-Ia) and Formula (IB-IIa), at theCF₃-oxadiazole motif. This dynamic equilibrium may be important for thebiological activity of the compounds of Formula (I), (respectively, asshown below) at the CF₃-oxadiazole motif. This dynamic equilibrium maybe important for the biological activity of the compounds of Formula(IA) and Formula (IB).

The designations of n, A¹, A², R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ andR¹⁰, with reference to the compounds of Formula (IA) and (IB) of thepresent invention apply generally to the compounds of Formula (IA-I) andFormula (IA-II), as well as to the specific disclosures of combinationsof n, A¹, A², R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰, as representedfor compounds of Formula (IA) in Tables 1.1A to 1.25A (below), or thecompounds 1.1 to 1.27 described in Table T1 (below).

Likewise, the designations of n, A¹, A², R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹ and R¹⁰, with reference to the compounds of Formula (IB) of thepresent invention apply generally to the compounds of Formula (IB-I) andFormula (IB-III), as well as to the specific disclosures of combinationsof n, A¹, A², R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰, as representedfor compounds of Formula (IB) in Tables 1.1B to 1.10B (below), or thecompounds 2.1 to 2.26 described in Table T2 (below).

Compounds of the present invention denoted generally for ease ofreference as compounds of Formula (I) encompassing compounds of bothFormula (IA) and Formula (IB), can be made as shown in the followingschemes 1 to 7, in which, unless otherwise stated, the definition ofeach variable is as defined herein for a compound of Formula (IA) orFormula (IB).

The compounds of Formula (I) can be obtained by an amide couplingtransformation with compounds of Formula (II) and compounds of Formula(III) by activating the carboxylic acid function of the compounds ofFormula (III), a process that usually takes place by converting the —OHof the carboxylic acid into a good leaving group, such as a chloridegroup, for example by using (COCl)₂ or SOCl₂, prior to treatment withthe compounds of Formula (IA), preferably in a suitable solvent (e.g.,dimethylformamide, dichloromethane or tetrahydrofuran), preferably at atemperature of between 25° C. and 100° C., and optionally in thepresence of a base such as triethylamine or N,N-diisopropylethylamine,or under conditions described in the literature for an amide coupling.For examples, see Valeur, E.; Bradley, M. Chem. Soc. Rev. (2009), 38,606 and Chinchilla, R., Najera, C. Chem. Soc. Rev. (2011), 40, 5084.Compounds of Formula (III) can be made by known methods from knowncompounds or are commercially available. For examples, see: Liu, K. etal. J. Med. Chem. (2008), 51, 7843 and WO 2013/008162 A1. Compounds ofFormula (II) are known compounds or are commercially available. This isshown in Scheme 1.

Alternatively, compounds of Formula (I) (R⁷ is not hydrogen) can beprepared from compounds of Formula (I) (R⁷ is hydrogen) and compounds ofFormula (IV), wherein X is chlorine, bromine or iodine, by treatmentwith a base (e.g., K₂CO₃ or Cs₂CO₃) in a suitable solvent, such asacetone or acetonitrile, at a temperature between 0° C. and 50° C. Forrelated examples, see Miyata, O et al. Tetrahedron (2004), 60, 3893.Compounds of Formula (IV) are known compounds or are commerciallyavailable. This is shown in Scheme 2

Alternatively, compounds of Formula (I) can be prepared from compoundsof Formula (V) by treatment with trifluoroacetic anhydride,trifluoroacetyl fluoride, or trifluoroacetyl chloride in a suitablesolvent, such as tetrahydrofuran, optionally in the presence of a base,such as pyridine, at a temperature between 0° C. and 25° C. For relatedexamples, see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268.This is shown in Scheme 3.

Compounds of Formula (V) can be prepared from compounds of Formula (VI)by treating them with a hydroxyamine hydrochloride salt in the presenceof a base, such as sodium carbonate, in a suitable solvent, such asmethanol, at a temperature between 0° C. and 100° C. For relatedexamples, see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268.This is shown in Scheme 4.

The compounds of Formula (VI) can be obtained by an amide couplingtransformation with compounds of Formula (II) and compounds of Formula(VII) by activating the carboxylic acid function of the compounds ofFormula (VII), a process that usually takes place by converting the —OHof the carboxylic acid into a good leaving group, such as a chloridegroup, for example by using (COCl)₂ or SOCl₂, prior to treatment withthe compounds of Formula (II), preferably in a suitable solvent (e.g.,dimethylformamide, dichloromethane or tetrahydrofuran), preferably at atemperature of between 25° C. and 100° C., and optionally in thepresence of a base such as triethylamine or N,N-diisopropylethylamine,or under conditions described in the literature for an amide coupling.For examples, see Valeur, E.; Bradley, M. Chem. Soc. Rev. (2009), 38,606 and Chinchilla, R., Najera, C. Chem. Soc. Rev. (2011), 40, 5084.This is shown in Scheme 5.

Compounds of Formula (III) can be prepared from compounds of Formula(VIII) by treatment with trifluoroacetic anhydride, trifluoroacetylfluoride, or trifluoroacetyl chloride in a suitable solvent, such astetrahydrofuran, optionally in the presence of a base, such as pyridine,at a temperature between 0° C. and 25° C. For related examples, seeKitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268. This is shown inScheme 6.

Compounds of Formula (VIII) can be prepared from compounds of Formula(VII) by treating them with a hydroxyamine hydrochloride salt in thepresence of a base, such as sodium carbonate, in a suitable solvent,such as methanol, at a temperature between 0° C. and 100° C. Compoundsof Formula (VIII) are commercially available. For related examples, seeKitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268. Compounds ofFormula (VII) are known compounds or are commercially available. This isshown in Scheme 7.

As already indicated, surprisingly, it has now been found that the novelcompounds of Formula (IA) and (IB) of the present invention have, forpractical purposes, a very advantageous level of biological activity forprotecting plants against diseases that are caused by fungi.

The compounds of Formula (IA) and (IB) can be used in the agriculturalsector and related fields of use, e.g., as active ingredients forcontrolling plant pests or on non-living materials for the control ofspoilage microorganisms or organisms potentially harmful to man. Thenovel compounds are distinguished by excellent activity at low rates ofapplication, by being well tolerated by plants and by beingenvironmentally safe. They have very useful curative, preventive andsystemic properties and can be used for protecting numerous cultivatedplants. The compounds of Formula (IA) and (IB) can be used to inhibit ordestroy the pests that occur on plants or parts of plants (fruit,blossoms, leaves, stems, tubers, roots) of different crops of usefulplants, while at the same time protecting also those parts of the plantsthat grow later, e.g., from phytopathogenic microorganisms.

The present invention further relates to a method for controlling orpreventing infestation of plants or plant propagation material and/orharvested food crops susceptible to microbial attack by treating plantsor plant propagation material and/or harvested food crops wherein aneffective amount a compound of Formula (IA) or (IB) is applied to theplants, to parts thereof or the locus thereof.

It is also possible to use compounds of Formula (IA) and (IB) asfungicides. The term “fungicide” as used herein means a compound thatcontrols, modifies, or prevents the growth of fungi. The term“fungicidally effective amount” where used means the quantity of such acompound or combination of such compounds that is capable of producingan effect on the growth of fungi. Controlling or modifying effectsinclude all deviation from natural development, such as killing,retardation and the like, and prevention includes barrier or otherdefensive formation in or on a plant to prevent fungal infection.

It may also be possible to use compounds of Formula (IA) and (IB)) asdressing agents for the treatment of plant propagation material, e.g.,seed, such as fruits, tubers or grains, or plant cuttings, for theprotection against fungal infections as well as against phytopathogenicfungi occurring in the soil. The propagation material can be treatedwith a composition comprising a compound of Formula (IA) or (IB) beforeplanting: seed, for example, can be dressed before being sown. Theactive compounds of Formula (IA) and (IB) can also be applied to grains(coating), either by impregnating the seeds in a liquid formulation orby coating them with a solid formulation. The composition can also beapplied to the planting site when the propagation material is beingplanted, for example, to the seed furrow during sowing. The inventionrelates also to such methods of treating plant propagation material andto the plant propagation material so treated.

Furthermore, the compounds of Formula (IA) and (IB) can be used forcontrolling fungi in related areas, for example in the protection oftechnical materials, including wood and wood related technical products,in food storage, in hygiene management.

In addition, the invention could be used to protect non-living materialsfrom fungal attack, e.g. lumber, wall boards and paint.

The compounds of Formula (IA) and (IB) are for example, effectiveagainst fungi and fungal vectors of disease as well as phytopathogenicbacteria and viruses. These fungi and fungal vectors of disease as wellas phytopathogenic bacteria and viruses are for example:

Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp,Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A.niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomycesdermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp.including B. dothidea, B. obtusa, Botrytis spp. inclusing B. cinerea,Candida spp. including C. albicans, C. glabrata, C. krusei, C.lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans,Ceratocystis spp, Cercospora spp. including C. arachidicola,Cercosporidium personatum, Cladosporium spp, Claviceps purpurea,Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C.musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechsleraspp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp.including E. cichoracearum, Eutypa lata, Fusarium spp. including F.culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum,F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis,Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum,Glomerella cingulate, Guignardia bidwellii, Gymnosporangiumjuniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasmaspp. including H. capsulatum, Laetisaria fuciformis, Leptographiumlindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochiumnivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp.including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostomapiceae, Paracoccidioides spp, Penicillium spp. including P. digitatum,P. italicum, Petriellidium spp, Peronosclerospora spp. Including P.maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaerianodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp,Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans,Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp.,Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxabetae, Pseudocercosporella herpotrichoides, Pseudomonas spp,Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopezizatracheiphila, Puccinia Spp. including P. hordei, P. recondita, P.striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp,Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum,Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus,Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S.prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp,Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis,Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp,Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephoruscucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp.including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp,Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturiaspp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

The compounds of Formula (IA) and (IB) may be used for example on turf,ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens,for example conifers, as well as for tree injection, pest management andthe like.

Within the scope of present invention, target crops and/or useful plantsto be protected typically comprise perennial and annual crops, such asberry plants for example blackberries, blueberries, cranberries,raspberries and strawberries; cereals for example barley, maize (corn),millet, oats, rice, rye, sorghum triticale and wheat; fibre plants forexample cotton, flax, hemp, jute and sisal; field crops for examplesugar and fodder beet, coffee, hops, mustard, oilseed rape (canola),poppy, sugar cane, sunflower, tea and tobacco; fruit trees for exampleapple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pearand plum; grasses for example Bermuda grass, bluegrass, bentgrass,centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass;herbs such as basil, borage, chives, coriander, lavender, lovage, mint,oregano, parsley, rosemary, sage and thyme; legumes for example beans,lentils, peas and soya beans; nuts for example almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio and walnut; palms for exampleoil palm; ornamentals for example flowers, shrubs and trees; othertrees, for example cacao, coconut, olive and rubber; vegetables forexample asparagus, aubergine, broccoli, cabbage, carrot, cucumber,garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin,rhubarb, spinach and tomato; and vines for example grapes.

The term “useful plants” is to be understood as also including usefulplants that have been rendered tolerant to herbicides like bromoxynil orclasses of herbicides (such as, for example, HPPD inhibitors, ALSinhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron,EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase)inhibitors) as a result of conventional methods of breeding or geneticengineering. An example of a crop that has been rendered tolerant toimidazolinones, e.g. imazamox, by conventional methods of breeding(mutagenesis) is Clearfield® summer rape (Canola). Examples of cropsthat have been rendered tolerant to herbicides or classes of herbicidesby genetic engineering methods include glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®.

The term “useful plants” is to be understood as also including usefulplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising one or more selectivelyacting toxins, such as are known, for example, from toxin-producingbacteria, especially those of the genus Bacillus.

Examples of such plants are: YieldGard® (maize variety that expresses aCryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses aCryIIIB(b1) toxin); YieldGard Plus® (maize variety that expresses aCryIA(b) and a CryIIIB(b1) toxin); Starlink® (maize variety thatexpresses a Cry9(c) toxin); Herculex I® (maize variety that expresses aCryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase(PAT) to achieve tolerance to the herbicide glufosinate ammonium);NuCOTN 33B® (cotton variety that expresses a CryIA(c) toxin); BollgardI® (cotton variety that expresses a CryIA(c) toxin); Bollgard II®(cotton variety that expresses a CryIA(c) and a CryIIA(b) toxin);VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potatovariety that expresses a CryIIIA toxin); NatureGard® Agrisure® GTAdvantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11corn borer (CB) trait), Agrisure® RW (corn rootworm trait) andProtecta®.

The term “crops” is to be understood as including also crop plants whichhave been so transformed by the use of recombinant DNA techniques thatthey are capable of synthesising one or more selectively acting toxins,such as are known, for example, from toxin-producing bacteria,especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins from Bacillus cereus or Bacilluspopilliae; or insecticidal proteins from Bacillus thuringiensis, such as8-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1,Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonisingnematodes, for example Photorhabdus spp. or Xenorhabdus spp., such asPhotorhabdus luminescens, Xenorhabdus nematophilus; toxins produced byanimals, such as scorpion toxins, arachnid toxins, wasp toxins and otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea lectins, barleylectins or snowdrop lectins; agglutinins; proteinase inhibitors, such astrypsin inhibitors, serine protease inhibitors, patatin, cystatin,papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolismenzymes, such as 3-hydroxysteroidoxidase,ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysoneinhibitors, HMG-COA-reductase, ion channel blockers, such as blockers ofsodium or calcium channels, juvenile hormone esterase, diuretic hormonereceptors, stilbene synthase, bibenzyl synthase, chitinases andglucanases.

Further, in the context of the present invention there are to beunderstood by 8-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2,Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins(Vip), for example Vip1, Vip2, Vip3 or Vip3A, expressly also hybridtoxins, truncated toxins and modified toxins. Hybrid toxins are producedrecombinantly by a new combination of different domains of thoseproteins (see, for example, WO 02/15701). Truncated toxins, for examplea truncated Cry1Ab, are known. In the case of modified toxins, one ormore amino acids of the naturally occurring toxin are replaced. In suchamino acid replacements, preferably non-naturally present proteaserecognition sequences are inserted into the toxin, such as, for example,in the case of Cry3A055, a cathepsin-G-recognition sequence is insertedinto a Cry3A toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO93/07278,WO95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. CryI-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated Cry1Ab toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a Cry1Ab toxin. Btl76 maize also transgenicallyexpresses the enzyme PAT to achieve tolerance to the herbicideglufosinate ammonium.3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCry3A toxin. This toxin is Cry3A055 modified by insertion of acathepsin-G-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, 5 Belgium, registration number C/DE/02/9. MON 863expresses a Cry3Bb1 toxin and has resistance to certain Coleopterainsects.5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein Cry1F for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603×MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium sp. strain CP4, which 20 imparts tolerance to theherbicide Roundup® (contains glyphosate), and also a Cry1Ab toxinobtained from Bacillus thuringiensis subsp. kurstaki which brings abouttolerance to certain Lepidoptera, include the European corn borer.

The term “locus” as used herein means fields in or on which plants aregrowing, or where seeds 25 of cultivated plants are sown, or where seedwill be placed into the soil. It includes soil, seeds, and seedlings, aswell as established vegetation.

The term “plants” refers to all physical parts of a plant, includingseeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, andfruits.

The term “plant propagation material” is understood to denote generativeparts of the plant, such as seeds, which can be used for themultiplication of the latter, and vegetative material, such as cuttingsor tubers, for example potatoes. There can be mentioned for exampleseeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes andparts of plants. Germinated plants and young plants which are to betransplanted after germination or after emergence from the soil, mayalso be mentioned. These young plants can be protected beforetransplantation by a total or partial treatment by immersion. Preferably“plant propagation material” is understood to denote seeds.

The compounds of Formula (IA) and (IB) may be used in unmodified formor, preferably, together with the adjuvants conventionally employed inthe art of formulation. To this end they may be conveniently formulatedin known manner to emulsifiable concentrates, coatable pastes, directlysprayable or dilutable solutions or suspensions, dilute emulsions,wettable powders, soluble powders, dusts, granulates, and alsoencapsulations e.g. in polymeric substances. As with the type of thecompositions, the methods of application, such as spraying, atomising,dusting, scattering, coating or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances. Thecompositions may also contain further adjuvants such as stabilizers,antifoams, viscosity regulators, binders or tackifiers as well asfertilizers, micronutrient donors or other formulations for obtainingspecial effects.

Suitable carriers and adjuvants, e.g. for agricultural use, can be solidor liquid and are substances useful in formulation technology, e.g.natural or regenerated mineral substances, solvents, dispersants,wetting agents, tackifiers, thickeners, binders or fertilizers. Suchcarriers are for example described in WO 97/33890.

Suspension concentrates are aqueous formulations in which finely dividedsolid particles of the active compound are suspended. Such formulationsinclude anti-settling agents and dispersing agents and may furtherinclude a wetting agent to enhance activity as well an anti-foam and acrystal growth inhibitor. In use, these concentrates are diluted inwater and normally applied as a spray to the area to be treated. Theamount of active ingredient may range from 0.5% to 95% of theconcentrate.

Wettable powders are in the form of finely divided particles whichdisperse readily in water or other liquid carriers. The particlescontain the active ingredient retained in a solid matrix. Typical solidmatrices include fuller's earth, kaolin clays, silicas and other readilywet organic or inorganic solids. Wettable powders normally contain from5% to 95% of the active ingredient plus a small amount of wetting,dispersing or emulsifying agent.

Emulsifiable concentrates are homogeneous liquid compositionsdispersible in water or other liquid and may consist entirely of theactive compound with a liquid or solid emulsifying agent, or may alsocontain a liquid carrier, such as xylene, heavy aromatic naphthas,isophorone and other non-volatile organic solvents. In use, theseconcentrates are dispersed in water or other liquid and normally appliedas a spray to the area to be treated. The amount of active ingredientmay range from 0.5% to 95% of the concentrate.

Granular formulations include both extrudates and relatively coarseparticles and are usually applied without dilution to the area in whichtreatment is required. Typical carriers for granular formulationsinclude sand, fuller's earth, attapulgite clay, bentonite clays,montmorillonite clay, vermiculite, perlite, calcium carbonate, brick,pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corncobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate,sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide,titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth,calcium sulphate and other organic or inorganic materials which absorbor which can be coated with the active compound. Granular formulationsnormally contain 5% to 25% of active ingredients which may includesurface-active agents such as heavy aromatic naphthas, kerosene andother petroleum fractions, or vegetable oils; and/or stickers such asdextrins, glue or synthetic resins.

Dusts are free-flowing admixtures of the active ingredient with finelydivided solids such as talc, clays, flours and other organic andinorganic solids which act as dispersants and carriers.

Microcapsules are typically droplets or granules of the activeingredient enclosed in an inert porous shell which allows escape of theenclosed material to the surroundings at controlled rates. Encapsulateddroplets are typically 1 to 50 microns in diameter. The enclosed liquidtypically constitutes 50 to 95% of the weight of the capsule and mayinclude solvent in addition to the active compound. Encapsulatedgranules are generally porous granules with porous membranes sealing thegranule pore openings, retaining the active species in liquid forminside the granule pores. Granules typically range from 1 millimetre to1 centimetre and preferably 1 to 2 millimetres in diameter. Granules areformed by extrusion, agglomeration or prilling, or are naturallyoccurring. Examples of such materials are vermiculite, sintered clay,kaolin, attapulgite clay, sawdust and granular carbon. Shell or membranematerials include natural and synthetic rubbers, cellulosic materials,styrene-butadiene copolymers, polyacrylonitriles, polyacrylates,polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

Other useful formulations for agrochemical applications include simplesolutions of the active ingredient in a solvent in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene and other organic solvents. Pressurisedsprayers, wherein the active ingredient is dispersed in finely-dividedform as a result of vaporisation of a low boiling dispersant solventcarrier, may also be used.

Suitable agricultural adjuvants and carriers that are useful informulating the compositions of the invention in the formulation typesdescribed above are well known to those skilled in the art.

Liquid carriers that can be employed include, for example, water,toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethylketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone,amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol,alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine,p-diethylbenzene, diethylene glycol, diethylene glycol abietate,diethylene glycol butyl ether, diethylene glycol ethyl ether, diethyleneglycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide,1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether,dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethylacetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1-trichloroethane,2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycolbutyl ether, ethylene glycol methyl ether, gamma-butyrolactone,glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate,hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate,isooctane, isophorone, isopropyl benzene, isopropyl myristate, lacticacid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamylketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyloleate, methylene chloride, m-xylene, n-hexane, n-octylamine,octadecanoic acid, octyl amine acetate, oleic acid, oleylamine,o-xylene, phenol, polyethylene glycol (PEG400), propionic acid,propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene,triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin,mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amylacetate, butyl acetate, methanol, ethanol, isopropanol, and highermolecular weight alcohols such as amyl alcohol, tetrahydrofurfuranylalcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol,glycerine and N-methyl-2-pyrrolidinone. Water is generally the carrierof choice for the dilution of concentrates.

Suitable solid carriers include, for example, talc, titanium dioxide,pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk,diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller'searth, cotton seed hulls, wheat flour, soybean flour, pumice, woodflour, walnut shell flour and lignin.

A broad range of surface-active agents are advantageously employed inboth said liquid and solid compositions, especially those designed to bediluted with carrier before application. These agents, when used,normally comprise from 0.1% to 15% by weight of the formulation. Theycan be anionic, cationic, non-ionic or polymeric in character and can beemployed as emulsifying agents, wetting agents, suspending agents or forother purposes. Typical surface active agents include salts of alkylsulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonatesalts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkyleneoxide addition products, such as nonylphenol-C.sub. 18 ethoxylate;alcohol-alkylene oxide addition products, such as tridecylalcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate;alkylnaphthalenesulfonate salts, such as sodiumdibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts,such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such assorbitol oleate; quaternary amines, such as lauryl trimethylammoniumchloride; polyethylene glycol esters of fatty acids, such aspolyethylene glycol stearate; block copolymers of ethylene oxide andpropylene oxide; and salts of mono and dialkyl phosphate esters.

Other adjuvants commonly utilized in agricultural compositions includecrystallisation inhibitors, viscosity modifiers, suspending agents,spray droplet modifiers, pigments, antioxidants, foaming agents,anti-foaming agents, light-blocking agents, compatibilizing agents,antifoam agents, sequestering agents, neutralising agents and buffers,corrosion inhibitors, dyes, odorants, spreading agents, penetrationaids, micronutrients, emollients, lubricants and sticking agents.

In addition, further, other biocidally active ingredients orcompositions may be combined with the compositions of the invention andused in the methods of the invention and applied simultaneously orsequentially with the compositions of the invention. When appliedsimultaneously, these further active ingredients may be formulatedtogether with the compositions of the invention or mixed in, forexample, the spray tank. These further biocidally active ingredients maybe fungicides, herbicides, insecticides, bactericides, acaricides,nematicides and/or plant growth regulators.

Pesticidal agents are referred to herein using their common name areknown, for example, from “The Pesticide Manual”, 15th Ed., British CropProtection Council 2009.

In addition, the compositions of the invention may also be applied withone or more systemically acquired resistance inducers (“SAR” inducer).SAR inducers are known and described in, for example, U.S. Pat. No.6,919,298 and include, for example, salicylates and the commercial SARinducer acibenzolar-S-methyl.

The compounds of Formula (IA) and (IB) are normally used in the form ofagrochemical compositions and can be applied to the crop area or plantto be treated, simultaneously or in succession with further compounds.These further compounds can be e.g. fertilizers or micronutrient donorsor other preparations, which influence the growth of plants. They canalso be selective herbicides or non-selective herbicides as well asinsecticides, fungicides, bactericides, nematicides, molluscicides ormixtures of several of these preparations, if desired together withfurther carriers, surfactants or application promoting adjuvantscustomarily employed in the art of formulation.

The compounds of Formula (IA) and (IB) may be used in the form of(fungicidal) compositions for controlling or protecting againstphytopathogenic microorganisms, comprising as active ingredient at leastone compound of Formula (IA) or (IB) or of at least one preferredindividual compound as defined herein, in free form or in agrochemicallyusable salt form, and at least one of the above-mentioned adjuvants.

The invention therefore provides a composition, preferably a fungicidalcomposition, comprising at least one compound of Formula (IA) or (IB),an agriculturally acceptable carrier and optionally an adjuvant. Anagricultural acceptable carrier is for example a carrier that issuitable for agricultural use. Agricultural carriers are well known inthe art. Preferably said composition may comprise at least one or morepesticidally-active compounds, for example an additional fungicidalactive ingredient in addition to the compound of Formula (IA) or (IB).

The compound of Formula (IA) or (IB) may be the sole active ingredientof a composition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may, in some cases, result in unexpected synergisticactivities.

Examples of suitable additional active ingredients include thefollowing: acycloamino acid fungicides, aliphatic nitrogen fungicides,amide fungicides, anilide fungicides, antibiotic fungicides, aromaticfungicides, arsenical fungicides, aryl phenyl ketone fungicides,benzamide fungicides, benzanilide fungicides, benzimidazole fungicides,benzothiazole fungicides, botanical fungicides, bridged diphenylfungicides, carbamate fungicides, carbanilate fungicides, conazolefungicides, copper fungicides, dicarboximide fungicides, dinitrophenolfungicides, dithiocarbamate fungicides, dithiolane fungicides, furamidefungicides, furanilide fungicides, hydrazide fungicides, imidazolefungicides, mercury fungicides, morpholine fungicides, organophosphorousfungicides, organotin fungicides, oxathiin fungicides, oxazolefungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazolefungicides, pyridine fungicides, pyrimidine fungicides, pyrrolefungicides, quaternary ammonium fungicides, quinoline fungicides,quinone fungicides, quinoxaline fungicides, strobilurin fungicides,sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides,thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides,triazine fungicides, triazole fungicides, triazolopyrimidine fungicides,urea fungicides, valinamide fungicides, and zinc fungicides.

Examples of suitable additional active ingredients also include thefollowing: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acidmethoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide,1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1),1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(4′-methylsulfanyl-biphenyl-2-yl)-amide,1-methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid[2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide,(5-Chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,(5-Bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,2-{2-[(E)-3-(2,6-Dichloro-phenyl)-1-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide,3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,(E)-N-methyl-2-[2-(2, 5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide,a-[N-(3-chloro-2, 6-xylyl)-2-methoxyacetamido]-y-butyrolactone,4-chloro-2-cyano-N, -dimethyl-5-p-tolylimidazole-1-sulfonamide,N-allyl-4, 5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide,N—(I-cyano-1, 2-dimethylpropyl)-2-(2, 4-dichlorophenoxy) propionamide,N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,(.+−.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol,2′,6′-dibromo-2-methyl-4-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,1-imidazolyl-1-(4′-chlorophenoxy)-3,3-dimethylbutan-2-one, methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate,methyl(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(phenyl-sulphonyloxy)phenoxy]phenyl-3-methoxyacrylate,methyl (E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl(E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate,methyl(E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate,methyl (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate,methyl (E)-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methoxyacrylate, methyl(E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-acrylate,methyl (E),(E)-2-{2-(3-methoxyphenyl)methyloximinomethyl]-phenyl}-3-methoxyacrylate, methyl(E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(4-chlorophenyl)-methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate,3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-en-5-ine),2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propinylalcohol, 4-chlorophenyl-3-iodopropargyl formal,3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallylalcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propinyln-butylcarbamate, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinylcyclohexyl-carbamate, 3-iodo-2-propinyl phenylcarbamate; phenolderivatives, such as tribromophenol, tetrachlorophenol,3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol,dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol,2-benzyl-4-chlorophenol, 5-hydroxy-2(5H)-furanone;4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone,4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one,3,5-dimethyl-tetrahydro-1,3,5-thiadiazine-2-thione,N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acypetacs,alanycarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradin,amisulbrom, amobam, ampropylfos, anilazine, asomate, aureofungin,azaconazole, azafendin, azithiram, azoxystrobin, barium polysulfide,benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron,benthiavalicarb, benthiazole, benzalkonium chloride, benzamacril,benzamorf, benzohydroxamic acid, benzovindiflupyr, berberine,bethoxazin, biloxazol, binapacryl, biphenyl, bitertanol, bithionol,bixafen, blasticidin-S, boscalid, bromothalonil, bromuconazole,bupirimate, buthiobate, butylamine calcium polysulfide, captafol,captan, carbamorph, carbendazim, carbendazim chlorhydrate, carboxin,carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chitosan,chlobenthiazone, chloraniformethan, chloranil, chlorfenazole, chloroneb,chloropicrin, chlorothalonil, chlorozolinate, chlozolinate, climbazole,clotrimazole, clozylacon, copper containing compounds such as copperacetate, copper carbonate, copper hydroxide, copper naphthenate, copperoleate, copper oxychloride, copper oxyquinolate, copper silicate, coppersulphate, copper tallate, copper zinc chromate and Bordeaux mixture,cresol, cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid,cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole,cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid,di-2-pyridyl disulphide 1, 1′-dioxide, dichlofluanid, diclomezine,dichlone, dicloran, dichlorophen, dichlozoline, diclobutrazol,diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim,O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetachlone,dimetconazole, dimethomorph, dimethirimol, diniconazole, diniconazole-M,dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon,diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon,dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin,dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole,etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethilicin, ethyl(Z)—N-benzyl-N([methyl (methyl-thioethylideneamino-oxycarbonyl) amino]thio)-ß-alaninate, etridiazole, famoxadone, fenamidone, fenaminosulf,fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan,fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph,fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, ferimzone,fluazinam, fludioxonil, flumetover, flumorph, flupicolide, fluopyram,fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole,flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet,formaldehyde, fosetyl, fuberidazole, furalaxyl, furametpyr, furcarbanil,furconazole, furfural, furmecyclox, furophanate, glyodin, griseofulvin,guazatine, halacrinate, hexa chlorobenzene, hexachlorobutadiene,hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen,hydroxyisoxazole, hymexazole, imazalil, imazalil sulphate,imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb,ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb,isopropanyl butyl carbamate, isoprothiolane, isopyrazam, isotianil,isovaledione, izopamfos, kasugamycin, kresoxim-methyl, LY186054,LY211795, LY248908, mancozeb, mandipropamid, maneb, mebenil,mecarbinzid, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil,mercuric chloride, mercurous chloride, meptyldinocap, metalaxyl,metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb,methfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate,metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax,milneb, moroxydine, myclobutanil, myclozolin, nabam, natamycin,neoasozin, nickel dimethyldithiocarbamate, nitrostyrene,nitrothal-iso-propyl, nuarimol, octhilinone, ofurace, organomercurycompounds, orysastrobin, osthol, oxadixyl, oxasulfuron, oxathiapiprolin,oxine-copper, oxolinic acid, oxpoconazole, oxycarboxin, parinol,pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol,penthiopyrad, phenamacril, phenazin oxide, phosdiphen, phosetyl-AI,phosphorus acids, phthalide, picoxystrobin, piperalin, polycarbamate,polyoxin D, polyoxrim, polyram, probenazole, prochloraz, procymidone,propamidine, propamocarb, propiconazole, propineb, propionic acid,proquinazid, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid,pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazophos,pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriofenone,pyroquilon, pyroxychlor, pyroxyfur, pyrrolnitrin, quaternary ammoniumcompounds, quinacetol, quinazamid, quinconazole, quinomethionate,quinoxyfen, quintozene, rabenzazole, santonin, sedaxane, silthiofam,simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine,streptomycin, sulphur, sultropen, tebuconazole, tebfloquin, tecloftalam,tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor,thicyofen, thifluzamide, 2-(thiocyanomethylthio) benzothiazole,thiophanate-methyl, thioquinox, thiram, tiadinil, timibenconazole,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triamiphos, triarimol, triazbutil, triazoxide, tricyclazole, tridemorph,trifloxystrobin, triflumazole, triforine, triflumizole, triticonazole,uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozolin,zarilamid, zineb, ziram, and zoxamide.

The compounds of the invention may also be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in U.S. Pat. No. 5,015,630,WO-9415944 and WO-9522552. Additional anthelmintic agents include thebenzimidazoles such as albendazole, cambendazole, fenbendazole,flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, andother members of the class. Additional anthelmintic agents includeimidazothiazoles and tetrahydropyrimidines such as tetramisole,levamisole, pyrantel pamoate, oxantel or morantel. Additionalanthelmintic agents include flukicides, such as triclabendazole andclorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat. Nos. 5,478,855, 4,639,771 and DE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO 96/15121 and also withanthelmintic active cyclic depsipeptides such as those described in WO96/11945, WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO94/19334, EP 0 382 173, and EP 0 503 538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in International PatentApplication Publication Numbers WO 95/19363 or WO 04/72086, particularlythe compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following:

Organophosphates: acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos,chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl,demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos,dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur,fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate,isoxathion, malathion, methacriphos, methamidophos, methidathion,methyl-parathion, mevinphos, monocrotophos, naled, omethoate,oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate,phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate,phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin,beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen,NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601,silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

The following mixtures of the compounds of Formula (IA) and (IB) withactive ingredients are preferred. The abbreviation “TX” means onecompound selected from the group consisting of the compounds describedin: Tables 1.1A to 1.25A or Table T1 (below); Tables 1.1B to 1.10B TableT2 (below).

an adjuvant selected from the group of substances consisting ofpetroleum oils (alternative name) (628)+TX,

an acaricide selected from the group of substances consisting of1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name)(1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name)(1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX,abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin(202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate(872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz(24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compoundcode)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin(46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternativename) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name)[CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX,brofenvalerate (alternative name)+TX, bromocyclen (918)+TX, bromophos(920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin(99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben(alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX,camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX,carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (developmentcode) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX,chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX,chlorfensulfide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate(975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX,chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl(146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II(696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel(alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternativename) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate(1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin(196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT(219)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S(1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O(1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX,demeton-S-methyl (224)+TX, demeton-S-methylsulfon (1039)+TX,diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX,dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternativename)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX,dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)(653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton(269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX,dinocton (1090)+TX, dino-penton (1092)+TX, dinosulfon (1097)+TX,dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPACname) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton(278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternativename) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX,eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX,ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX,fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternativename)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil(1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim(360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron(366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron(370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate(1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX,formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate(1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX,heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/ChemicalAbstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPACname) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropylO-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II(696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX,malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan(1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX,methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX,methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX,mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX,milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512(compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternativename) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloridecomplex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compoundcode)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX,oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX,permethrin (626)+TX, petroleum oils (alternative name) (628)+TX,phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX,phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes(traditional name) (1347)+TX, polynactins (alternative name) (653)+TX,proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite(671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion(1360)+TX, prothoate (1362)+TX, pyrethrin I (696)+TX, pyrethrin II(696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos(711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX,RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan(1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name)[CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen(738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep(753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX,tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam(alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX,tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox(alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX,thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternativename) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos(820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion(847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX,

an algicide selected from the group of substances consisting ofbethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX, coppersulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen(232)+TX, endothal (295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX,nabam (566)+TX, quinoclamine (714)+TX, quinonamid (1379)+TX, simazine(730)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltinhydroxide (IUPAC name) (347)+TX,

an anthelmintic selected from the group of substances consisting ofabamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name)[CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin(alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX,milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternativename) [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)[CCN]+TX, spinosad (737) and thiophanate (1435)+TX,

an avicide selected from the group of substances consisting ofchloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,

a bactericide selected from the group of substances consisting of1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copperdioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name)(169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione(1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde(404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin(483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickelbis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin(580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline(611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole(658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX,

a biological agent selected from the group of substances consisting ofAdoxophyes orana GV (alternative name) (12)+TX, Agrobacteriumradiobacter (alternative name) (13)+TX, Amblyseius spp. (alternativename) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX,Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis(alternative name) (33)+TX, Aphidius colemani (alternative name)(34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographacalifornica NPV (alternative name) (38)+TX, Bacillus firmus (alternativename) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX,Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillusthuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillusthuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillusthuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveriabassiana (alternative name) (53)+TX, Beauveria brongniartii (alternativename) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonellaGV (alternative name) (191)+TX, Dacnusa sibirica (alternative name)(212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa(scientific name) (293)+TX, Eretmocerus eremicus (alternative name)(300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX,Heterorhabditis bacteriophora and H. megidis (alternative name)(433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastixdactylopii (alternative name) (488)+TX, Macrolophus caliginosus(alternative name) (491)+TX, Mamestra brassicae NPV (alternative name)(494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhiziumanisopliae var. acridum (scientific name) (523)+TX, Metarhiziumanisopliae var. anisopliae (scientific name) (523)+TX, Neodiprionsertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp.(alternative name) (596)+TX, Paecilomyces fumosoroseus (alternativename) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX,Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientificname) (741)+TX, Steinernema bibionis (alternative name) (742)+TX,Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae(alternative name) (742)+TX, Steinernema glaseri (alternative name)(742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernemariobravis (alternative name) (742)+TX, Steinernema scapterisci(alternative name) (742)+TX, Steinernema spp. (alternative name)(742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhlodromusoccidentalis (alternative name) (844) and Verticillium lecanii(alternative name) (848)+TX, Bacillus subtilis var. amyloliquefaciensStrain FZB24 (available from Novozymes Biologicals Inc., 5400 CorporateCircle, Salem, Va. 24153, U.S.A. and known under the trade nameTaegro®)+TX,

a soil sterilant selected from the group of substances consisting ofiodomethane (IUPAC name) (542) and methyl bromide (537)+TX,

a chemosterilant selected from the group of substances consisting ofapholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan(alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif(alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa[CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid[CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX,thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name)[CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternativename) [CCN]+TX,

an insect pheromone selected from the group of substances consisting of(E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222)+TX,(E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX,(E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,(E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,(Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal(IUPAC name) (436)+TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name)(437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,(Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al(IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,(Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,(7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,(9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,(9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin(alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX,codlelure (alternative name) [CCN]+TX, codlemone (alternative name)(167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX,dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate(IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate (IUPAC name)(284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name)[CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternativename) (420)+TX, grandlure (421)+TX, grandlure I (alternative name)(421)+TX, grandlure II (alternative name) (421)+TX, grandlure III(alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX,hexalure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol(alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX,lineatin (alternative name) [CCN]+TX, litlure (alternative name)[CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX,megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternativename) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate(IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name)(589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternativename) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX,sordidin (alternative name) (736)+TX, sulcatol (alternative name)[CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure(839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure B₁(alternative name) (839)+TX, trimedlure B₂ (alternative name) (839)+TX,trimedlure C (alternative name) (839) and trunc-call (alternative name)[CCN]+TX,

an insect repellent selected from the group of substances consisting of2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX,butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPAC name)(1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name)(1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX,dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide[CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX,oxamate [CCN] and picaridin [CCN]+TX,

an insecticide selected from the group of substances consisting of1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058)+TX,1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX,1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX,1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX,2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)(1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate(IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate(IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethylthiocyanate (IUPAC/Chemical Abstracts name) (935)+TX,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ChemicalAbstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name)(986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione(IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate(IUPAC name) (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name)(1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX,4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name)(1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPACname) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX,acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX,aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate(872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate(875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin(alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl(44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillusthuringiensis delta endotoxins (alternative name) (52)+TX, bariumhexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide(IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer22/190 (development code) (893)+TX, Bayer 22408 (development code)(894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX,beta-cyfluthrin (194)+TX, beta-cypermethrin (203)+TX, bifenthrin(76)+TX, bioallethrin (78)+TX, bioallethrin S-cyclopentenyl isomer(alternative name) (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin(908)+TX, bioresmethrin (80)+TX, bis(2-chloroethyl) ether (IUPAC name)(909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate(alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen (918)+TX,bromo-DDT (alternative name) [CCN]+TX, bromophos (920)+TX,bromophos-ethyl (921)+TX, bufencarb (924)+TX, buprofezin (99)+TX,butacarb (926)+TX, butathiofos (927)+TX, butocarboxim (103)+TX, butonate(932)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbondisulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride(IUPAC name) (946)+TX, carbophenothion (947)+TX, carbosulfan (119)+TX,cartap (123)+TX, cartap hydrochloride (123)+TX, cevadine (alternativename) (725)+TX, chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone(963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos(131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform[CCN]+TX, chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos(990)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX,chlorthiophos (994)+TX, chromafenozide (150)+TX, cinerin I (696)+TX,cinerin II (696)+TX, cinerins (696)+TX, cis-resmethrin (alternativename)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate[CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, coumithoate(1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos(1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS708 (development code) (1012)+TX, cyanofenphos (1019)+TX, cyanophos(184)+TX, cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin(188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX, cypermethrin(201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate(alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX,d-tetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet(216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX,demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX,demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX,demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl(224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon(1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos(alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos(243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron(250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX,dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin(1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex(1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam(1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan(1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion(1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX,doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone(alternative name) [CCN]+TX, El 1642 (development code) (1118)+TX,emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin(1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX,eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX,etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion(309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos(312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternativename) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride(chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos(326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb(1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb(336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin(1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX,fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX,fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX,flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX,flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX,flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code)(1185)+TX, fonofos (1191)+TX, formetanate (405)+TX, formetanatehydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate (408)+TX,fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin (1200)+TX,gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine (422)+TX,guazatine acetates (422)+TX, GY-81 (development code) (423)+TX,halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD(1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos[CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX,hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX,iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX,isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin(1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX,isopropyl O-(methoxy-aminothiophosphoryl)salicylate (IUPAC name)(473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion(480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I(alternative name) [CCN]+TX, juvenile hormone II (alternative name)[CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX, kelevan(1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, leadarsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane(430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion(1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesiumphosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben(1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX,mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX,metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX,methacrifos (1266)+TX, methamidophos (527)+TX, methanesulfonyl fluoride(IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX,methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX,methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternativename) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methylbromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform(alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin[CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos(556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime(alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX,naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170(development code) (1306)+TX, NC-184 (compound code)+TX, nicotine(578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram(579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250(compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron(585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethylO-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name)(1074)+TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyldithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name)(593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemeton-methyl(609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT(219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,parathion-methyl (616)+TX, penfluron (alternative name) [CCN]+TX,pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name)(623)+TX, permethrin (626)+TX, petroleum oils (alternative name)(628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX,phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX,phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX,pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX,polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX,polychloroterpenes (traditional name) (1347)+TX, potassium arsenite[CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX,precocene I (alternative name) [CCN]+TX, precocene II (alternative name)[CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos(1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl(1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos(673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos(686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine(688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin(1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins(696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen(708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX,quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX,R-1492 (development code) (1382)+TX, rafoxanide (alternative name)[CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (developmentcode) (723)+TX, RU 25475 (development code) (1386)+TX, ryania(alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX,sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos(alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009(compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compoundcode)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129(development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide(444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX,sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide(623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate[CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX,spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX,sulfluramid (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX,sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX,teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP(1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX,terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos(777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX,thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam(792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam(798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap(803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name)[CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin(813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate(818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX,trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine(alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302(compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternativename)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901(development code) (858)+TX, cyantraniliprole [736994-63-19+TX,chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX,cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX,spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX,sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin[915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX, triflumezopyrim(disclosed in WO 2012/092115)+TX,

a molluscicide selected from the group of substances consisting ofbis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX,calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite[CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate(IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX,niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol(623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX,thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) andtriphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole[394730-71-3]+TX, a nematicide selected from the group of substancesconsisting of AKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane(IUPAC/Chemical Abstracts name) (1045)+TX, 1,2-dichloropropane(IUPAC/Chemical Abstracts name) (1062)+TX, 1,2-dichloropropane with1,3-dichloropropene (IUPAC name) (1063)+TX, 1,3-dichloropropene(233)+TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/ChemicalAbstracts name) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPACname) (980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid(IUPAC name) (1286)+TX, 6-isopentenylaminopurine (alternative name)(210)+TX, abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX,aldicarb (16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX,benclothiaz [CCN]+TX, benomyl (62)+TX, butylpyridaben (alternativename)+TX, cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide(945)+TX, carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos(145)+TX, cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX,dazomet (216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX,dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate(262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX,fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate(408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX,GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane(IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,ivermectin (alternative name) [CCN]+TX, kinetin (alternative name)(210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium(alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide(537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternativename) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrotheciumverrucaria composition (alternative name) (565)+TX, NC-184 (compoundcode)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX,phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin(alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternativename)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/ChemicalAbstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin(1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name)(210)+TX, fluensulfone [318290-98-1]+TX,

a nitrification inhibitor selected from the group of substancesconsisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,

a plant activator selected from the group of substances consisting ofacibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) andReynoutria sachalinensis extract (alternative name) (720)+TX,

a rodenticide selected from the group of substances consisting of2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu(880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX,bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX,bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX,chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX,coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX,fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadinehydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogencyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX,magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX,norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name)(640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite[CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite[CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX,strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zincphosphide (640)+TX,

a synergist selected from the group of substances consisting of2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX,5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX,farnesol with nerolidol (alternative name) (324)+TX, MB-599 (developmentcode) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide(649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (developmentcode) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide(1406)+TX,

an animal repellent selected from the group of substances consisting ofanthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX,copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene(chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates(422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX,thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram(856)+TX,

a virucide selected from the group of substances consisting of imanin(alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,

a wound protectant selected from the group of substances consisting ofmercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl(802)+TX,

and biologically active compounds selected from the group consisting ofametoctradin [865318-97-4]+TX, amisulbrom [348635-87-0]+TX, azaconazole[60207-31-0]+TX, benzovindiflupyr [1072957-71-1]+TX, bitertanol[70585-36-3]+TX, bixafen [581809-46-3]+TX, bromuconazole[116255-48-2]+TX, coumoxystrobin [850881-70-8]+TX, cyproconazole[94361-06-5]+TX, difenoconazole [119446-68-3]+TX, diniconazole[83657-24-3]+TX, enoxastrobin [238410-11-2]+TX, epoxiconazole[106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fenpyrazamine[473798-59-3]+TX, fluquinconazole [136426-54-5]+TX, flusilazole[85509-19-9]+TX, flutriafol [76674-21-0]+TX, fluxapyroxad[907204-31-3]+TX, fluopyram [658066-35-4]+TX, fenaminstrobin[366815-39-6]+TX, isofetamid [875915-78-9]+TX, hexaconazole[79983-71-4]+TX, imazalil [35554-44-0]+TX, imiben-conazole[86598-92-7]+TX, ipconazole [125225-28-7]+TX, ipfentrifluconazole[1417782-08-1]+TX, isotianil [224049-04-1]+TX, mandestrobin[173662-97-0] (can be prepared according to the procedures described inWO 2010/093059)+TX, mefentrifluconazole [1417782-03-6]+TX, metconazole[125116-23-6]+TX, myclobutanil [88671-89-0]+TX, paclobutrazol[76738-62-0]+TX, pefurazoate [101903-30-4]+TX, penflufen[494793-67-8]+TX, penconazole [66246-88-6]+TX, prothioconazole[178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX,propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX,tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX,triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole[99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol[12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX,bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidin [67306-00-7]+TX,fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph[81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim[110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil[74738-17-3]+TX, fludioxonil [131341-86-1]+TX, fluindapyr[1383809-87-7]+TX, benalaxyl [71626-11-4]+TX, furalaxyl [57646-30-7]+TX,metalaxyl [57837-19-1]+TX, R-metalaxyl [70630-17-0]+TX, ofurace[58810-48-3]+TX, oxadixyl [77732-09-3]+TX, benomyl [17804-35-2]+TX,carbendazim [10605-21-7]+TX, debacarb [62732-91-6]+TX, fuberidazole[3878-19-1]+TX, thiabendazole [148-79-8]+TX, chlozolinate[84332-86-5]+TX, dichlozoline [24201-58-9]+TX, iprodione[36734-19-7]+TX, myclozoline [54864-61-8]+TX, procymidone[32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid[188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX,flutolanil [66332-96-5]+TX, flutianil [958647-10-4]+TX, mepronil[55814-41-0]+TX, oxycarboxin [5259-88-1]+TX, penthiopyrad[183675-82-3]+TX, thifluzamide [130000-40-7]+TX, guazatine[108173-90-6]+TX, dodine [2439-10-3] [112-65-2] (free base)+TX,iminoctadine [13516-27-3]+TX, azoxystrobin [131860-33-8]+TX,dimoxystrobin [149961-52-4]+TX, enestroburin {Proc. BCPC, Int. Congr.,Glasgow, 2003, 1, 93}+TX, fluoxastrobin [361377-29-9]+TX,kresoxim-methyl [143390-89-0]+TX, metominostrobin [133408-50-1]+TX,trifloxystrobin [141517-21-7]+TX, orysastrobin [248593-16-0]+TX,picoxystrobin [117428-22-5]+TX, pyraclostrobin [175013-18-0]+TX,pyraoxystrobin [862588-11-2]+TX, ferbam [14484-64-1]+TX, mancozeb[8018-01-7]+TX, maneb [12427-38-2]+TX, metiram [9006-42-2]+TX, propineb[12071-83-9]+TX, thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram[137-30-4]+TX, captafol [2425-06-1]+TX, captan [133-06-2]+TX,dichlofluanid [1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet[133-07-3]+TX, tolylfluanid [731-27-1]+TX, bordeaux mixture[8011-63-0]+TX, copperhydroxid [20427-59-2]+TX, copperoxychlorid[1332-40-7]+TX, coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX,mancopper [53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap[131-72-6]+TX, nitrothal-isopropyl [10552-74-6]+TX, edifenphos[17109-49-8]+TX, iprobenphos [26087-47-8]+TX, isoprothiolane[50512-35-1]+TX, phosdiphen [36519-00-3]+TX, pyrazophos [13457-18-6]+TX,tolclofos-methyl [57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX,anilazine [101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX,chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil[57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX,diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb[87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-L190 (Flumorph)[211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX,etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone[161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX,ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide[239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol[10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid)[120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide [27355-22-2]+TX, picarbutrazox[500207-04-5]+TX, polyoxins [11113-80-7]+TX, probenazole[27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid[189278-12-4]+TX, pydiflumetofen [1228284-64-7]+TX, pyrametostrobin[915410-70-7]+TX, pyroquilon [57369-32-1]+TX, pyriofenone[688046-61-9]+TX, pyribencarb [799247-52-2]+TX, pyrisoxazole[847749-37-5]+TX, quinoxyfen [124495-18-7]+TX, quintozene [82-68-8]+TX,sulfur [7704-34-9]+TX, Timorex Gold™ (plant extract containing tea treeoil from the Stockton Group)+TX, tebufloquin [376645-78-2]+TX, tiadinil[223580-51-6]+TX, triazoxide [72459-58-6]+TX, tolprocarb[911499-62-2]+TX, triclopyricarb [902760-40-1]+TX, tricyclazole[41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX,valifenalate [283159-90-0]+TX, zoxamide (RH7281) [156052-68-5]+TX,mandipropamid [374726-62-2]+TX, isopyrazam [881685-58-1]+TX,phenamacril+TX, sedaxane [874967-67-6]+TX, trinexapac-ethyl[95266-40-3]+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide(dislosed in WO 2007/048556)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO2006/087343)+TX,[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate[915972-17-7]+TX and1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide[926914-55-8]+TX,

or a biologically active compound selected from the group consisting ofN-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide(can be prepared according to the procedures described in WO2010/130767)+TX,2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone(can be prepared according to the procedures described in WO2011/138281)+TX,6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile+TX,4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine(can be prepared according to the procedures described in WO2012/031061)+TX,3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide(can be prepared according to the procedures described in WO2012/084812)+TX, CAS 850881-30-0+TX,3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole 1,1-dioxide(can be prepared according to the procedures described in WO2007/129454)+TX,2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide+TX,3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone (canbe prepared according to the procedures described in WO 2005/070917)+TX,2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol (canbe prepared according to the procedures described in WO 2011/081174)+TX,2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol(can be prepared according to the procedures described in WO2011/081174)+TX, oxathiapiprolin+TX [1003318-67-9], tert-butylN-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate+TX,N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide(can be prepared according to the procedures described in WO2007/072999)+TX,3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide(can be prepared according to the procedures described in WO2014/013842)+TX, 2,2,2-trifluoroethylN-[2-methyl-1-[[(4-methylbenzoyl)amino]methyl]propyl]carbamate+TX,(2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol+TX,(2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol+TX,2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX,N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+TX,N′-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine(can be prepared according to the procedures described in WO2007/031513)+TX,[2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate (can be prepared according to the procedures describedin WO 2012/025557)+TX, but-3-ynylN-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate(can be prepared according to the procedures described in WO2010/000841)+TX,2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-triazole-3-thione(can be prepared according to the procedures described in WO2010/146031)+TX, methylN-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate+TX,3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (can beprepared according to the procedures described in WO 2005/121104)+TX,2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol(can be prepared according to the procedures described in WO2013/024082)+TX,3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (can beprepared according to the procedures described in WO 2012/020774)+TX,4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile (canbe prepared according to the procedures described in WO 2012/020774)+TX,(R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide(can be prepared according to the procedures described in WO2011/162397)+TX,3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide(can be prepared according to the procedures described in WO2012/084812)+TX,1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one(can be prepared according to the procedures described in WO2013/162072)+TX,1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one(can be prepared according to the procedures described in WO2014/051165)+TX,(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide+TX,(4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate+TX,N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide[1255734-28-1] (can be prepared according to the procedures described inWO 2010/130767)+TX,3-(difluoromethyl)-N—[(R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazole-4-carboxamide[1352994-67-2]+TX,N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+TX,N′-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine+TX,N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+TX,N′-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine+TX,

(fenpicoxamid [517875-34-2])+TX (as described in WO 2003/035617),2-(difluoromethyl)-N-(1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX,and2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide+TX,wherein each of these carboxamide compounds can be prepared according tothe procedures described in WO 2014/095675 and/or WO 2016/139189.

The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. The abovedescribed mixing partners are known. Where the active ingredients areincluded in “The Pesticide Manual” [The Pesticide Manual—A WorldCompendium; Thirteenth Edition; Editor: C. D. S. TomLin; The BritishCrop Protection Council], they are described therein under the entrynumber given in round brackets hereinabove for the particular compound;for example, the compound “abamectin” is described under entry number(1). Where “[CCN]” is added hereinabove to the particular compound, thecompound in question is included in the “Compendium of Pesticide CommonNames”, which is accessible on the internet [A. Wood; Compendium ofPesticide Common Names, Copyright © 1995-2004]; for example, thecompound “acetoprole” is described under the internet addresshttp://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “develoment code” isused or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The active ingredient mixture of the compounds of Formula (IA) or (IB)selected from a compound 1.1 to 1.27 described in Table T1 (below), or acompound 2.1 to 2.26 described in Table T2 (below) and an activeingredient as described above are preferably in a mixing ratio of from100:1 to 1:6000, especially from 50:1 to 1:50, more especially in aratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, veryespecially from 5:1 and 1:5, special preference being given to a ratioof from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewisepreferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4,or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5,or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75,or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750,or 2:750, or 4:750. Those mixing ratios are by weight.

The mixtures as described above can be used in a method for controllingpests, which comprises applying a composition comprising a mixture asdescribed above to the pests or their environment, with the exception ofa method for treatment of the human or animal body by surgery or therapyand diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of Formula (IA) or (IB) selected fromone of Tables 1.1A to 1.25A, 1.1B to 1.10B (below), or Table T1 or T2(below), and one or more active ingredients as described above can beapplied, for example, in a single “ready-mix” form, in a combined spraymixture composed from separate formulations of the single activeingredient components, such as a “tank-mix”, and in a combined use ofthe single active ingredients when applied in a sequential manner, i.e.one after the other with a reasonably short period, such as a few hoursor days. The order of applying the compounds of Formula (IA) or (IB)selected from Tables 1.1A to 1.25A, 1.1B to 1.10B (below), or Table T1or T2 (below), and the active ingredient(s) as described above, is notessential for working the present invention.

The compositions according to the invention can also comprise furthersolid or liquid auxiliaries, such as stabilizers, for exampleunepoxidized or epoxidized vegetable oils (for example epoxidizedcoconut oil, rapeseed oil or soya oil), antifoams, for example siliconeoil, preservatives, viscosity regulators, binders and/or tackifiers,fertilizers or other active ingredients for achieving specific effects,for example bactericides, fungicides, nematocides, plant activators,molluscicides or herbicides.

The compositions according to the invention are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds of Formula (IA) or (IB) for the preparation of thesecompositions are also a subject of the invention.

Another aspect of the invention is related to the use of a compound ofFormula (IA) or (IB) or of a preferred individual compound as definedherein, of a composition comprising at least one compound of Formula(IA) or (IB) or at least one preferred individual compound asabove-defined, or of a fungicidal or insecticidal mixture comprising atleast one compound of Formula (IA) or (IB) or at least one preferredindividual compound as above-defined, in admixture with other fungicidesor insecticides as described above, for controlling or preventinginfestation of plants, e.g. useful plants such as crop plants,propagation material thereof, e.g. seeds, harvested crops, e.g.harvested food crops, or non-living materials by insects or byphytopathogenic microorganisms, preferably fungal organisms.

A further aspect of the invention is related to a method of controllingor preventing an infestation of plants, e.g., useful plants such as cropplants, propagation material thereof, e.g. seeds, harvested crops, e.g.,harvested food crops, or of non-living materials by insects or byphytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, which comprises theapplication of a compound of Formula (IA) or (IB) or of a preferredindividual compound as above-defined as active ingredient to the plants,to parts of the plants or to the locus thereof, to the propagationmaterial thereof, or to any part of the non-living materials.

Controlling or preventing means reducing infestation by phytopathogenicor spoilage microorganisms or organisms potentially harmful to man,especially fungal organisms, to such a level that an improvement isdemonstrated.

A preferred method of controlling or preventing an infestation of cropplants by phytopathogenic microorganisms, especially fungal organisms,or insects which comprises the application of a compound of Formula (IA)or (IB), or an agrochemical composition which contains at least one ofsaid compounds, is foliar application. The frequency of application andthe rate of application will depend on the risk of infestation by thecorresponding pathogen or insect. However, the compounds of Formula (IA)and (IB) can also penetrate the plant through the roots via the soil(systemic action) by drenching the locus of the plant with a liquidformulation, or by applying the compounds in solid form to the soil,e.g. in granular form (soil application). In crops of water rice suchgranulates can be applied to the flooded rice field. The compounds ofFormula (IA) and (IB) may also be applied to seeds (coating) byimpregnating the seeds or tubers either with a liquid formulation of thefungicide or coating them with a solid formulation.

A formulation, e.g. a composition containing the compound of Formula(IA) or (IB), and, if desired, a solid or liquid adjuvant or monomersfor encapsulating the compound of Formula (IA) or (IB), may be preparedin a known manner, typically by intimately mixing and/or grinding thecompound with extenders, for example solvents, solid carriers and,optionally, surface active compounds (surfactants).

Advantageous rates of application are normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kga.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seeddrenching agent, convenient dosages are from 10 mg to 1 g of activesubstance per kg of seeds.

When the combinations of the present invention are used for treatingseed, rates of 0.001 to 50 g of a compound of Formula (IA) or (IB) perkg of seed, preferably from 0.01 to 10 g per kg of seed are generallysufficient.

Suitably, a composition comprising a compound of Formula (IA) or (IB)according to the present invention is applied either preventative,meaning prior to disease development or curative, meaning after diseasedevelopment.

The compositions of the invention may be employed in any conventionalform, for example in the form of a twin pack, a powder for dry seedtreatment (DS), an emulsion for seed treatment (ES), a flowableconcentrate for seed treatment (FS), a solution for seed treatment (LS),a water dispersible powder for seed treatment (WS), a capsule suspensionfor seed treatment (CF), a gel for seed treatment (GF), an emulsionconcentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE),a capsule suspension (CS), a water dispersible granule (WG), anemulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion,oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oilmiscible flowable (OF), an oil miscible liquid (OL), a solubleconcentrate (SL), an ultra-low volume suspension (SU), an ultra-lowvolume liquid (UL), a technical concentrate (TK), a dispersibleconcentrate (DC), a wettable powder (WP) or any technically feasibleformulation in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in conventional manner, e.g. by mixingthe active ingredients with appropriate formulation inerts (diluents,solvents, fillers and optionally other formulating ingredients such assurfactants, biocides, anti-freeze, stickers, thickeners and compoundsthat provide adjuvancy effects). Also conventional slow releaseformulations may be employed where long lasting efficacy is intended.Particularly formulations to be applied in spraying forms, such as waterdispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like),wettable powders and granules, may contain surfactants such as wettingand dispersing agents and other compounds that provide adjuvancyeffects, e.g. the condensation product of formaldehyde with naphthalenesulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkylsulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

A seed dressing formulation is applied in a manner known per se to theseeds employing the combination of the invention and a diluent insuitable seed dressing formulation form, e.g. as an aqueous suspensionor in a dry powder form having good adherence to the seeds. Such seeddressing formulations are known in the art. Seed dressing formulationsmay contain the single active ingredients or the combination of activeingredients in encapsulated form, e.g. as slow release capsules ormicrocapsules.

In general, the formulations include from 0.01 to 90% by weight ofactive agent, from 0 to 20% agriculturally acceptable surfactant and 10to 99.99% solid or liquid formulation inerts and adjuvant(s), the activeagent consisting of at least the compound of Formula (IA) or (IB)optionally together with other active agents, particularly microbiocidesor conservatives or the like. Concentrated forms of compositionsgenerally contain in between about 2 and 80%, preferably between about 5and 70% by weight of active agent. Application forms of formulation mayfor example contain from 0.01 to 20% by weight, preferably from 0.01 to5% by weight of active agent. Whereas commercial products willpreferably be formulated as concentrates, the end user will normallyemploy diluted formulations.

Whereas it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

Table 1.1A:

This table discloses 25 specific compounds of the formula (T-1A):

wherein n is 0, A¹ is C—R¹, A² is C—R², and R², R³, R⁴, and R⁸ arehydrogen, R¹ is fluorine, and R⁷ is as defined below in the Table 1A.

Each of Tables 1.2A to 1.25A (which follow Table 1A) make available 25individual compounds of the formula (T-1A) in which n, A¹, A², R¹, R²,R³, R⁴, R⁵, R⁶, and R⁸ are as specifically defined in Tables 1.2A to1.25A, which refer to Table 1A wherein R⁷ is specifically defined.

TABLE 1A Compound No. R⁷ 1A.001 H 1A.002 methyl 1A.003 ethyl 1A.004propyl 1A.005 isopropyl 1A.006 cyclopropyl 1A.007 butyl 1A.008 allyl1A.009 propargyl 1A.010 3,3-dichloroallyl 1A.011 2-hydroxyethyl 1A.0122-hydroxypropyl 1A.013 2-methoxyethyl 1A.014 2-difluoromethoxyethyl1A.015 2-methoxypropyl 1A.016 2-hydroxy-1-methyl-ethyl 1A.0172-methoxy-1-methyl-ethyl 1A.018 2-difluoromethoxy-1-methyl-ethyl 1A.019methyl 2-acetate 1A.020 methyl 2-propanoate 1A.0212-(tert-butylamino)-2-oxo-ethyl 1A.022 cyclopropylmethyl 1A.023 phenyl1A.024 benzyl 1A.025 2-furanylmethylTable 1.2A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R², R³, and R⁴ are hydrogen, R¹ isfluorine, R⁸ is methyl, and R⁷ is as defined above in the Table 1A.

Table 1.3A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R², R³, and R⁴ are hydrogen, R¹ isfluorine, R⁸ is allyl, and R⁷ is as defined above in the Table 1A.

Table 1.4A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R², R³, and R⁴ are hydrogen, R¹ isfluorine, R⁸ is propargyl, and R⁷ is as defined above in the Table 1A.

Table 1.5A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R², R³, and R⁴ are hydrogen, R¹ isfluorine, R⁸ is benzyl, and R⁷ is as defined above in the Table 1A.

Table 1.6A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², R⁴, and R⁸ are hydrogen, R³ isfluorine, and R⁷ is as defined above in the Table 1A.

Table 1.7A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², and R⁴ are hydrogen, R³ isfluorine, R⁸ is methyl, and R⁷ is as defined above in the Table 1A.

Table 1.8A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², and R⁴ are hydrogen, R³ isfluorine, R⁸ is allyl, and R⁷ is as defined above in the Table 1A.

Table 1.9A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², and R⁴ are hydrogen, R³ isfluorine, R⁸ is propargyl, and R⁷ is as defined above in the Table 1A.

Table 1.10A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², and R⁴ are hydrogen, R³ isfluorine, R⁸ is benzyl, and R⁷ is as defined above in the Table 1A.

Table 1.11A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R³, R⁴, and R⁸ are hydrogen, R¹ and R²are fluorine, and R⁷ is as defined above in the Table 1A.

Table 1.12A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R³ and R⁴ are hydrogen, R¹ and R² arefluorine, R⁸ is methyl, and R⁷ is as defined above in the Table 1A.

Table 1.13A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R³ and R⁴ are hydrogen, R¹ and R² arefluorine, R⁸ is allyl, and R⁷ is as defined above in the Table 1A.

Table 1.14A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R³ and R⁴ are hydrogen, R¹ and R² arefluorine, R⁸ is propargyl, and R⁷ is as defined above in the Table 1A.

Table 1.15A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is C—R¹, A² is C—R², and R³ and R⁴ are hydrogen, R¹ and R² arefluorine, R⁸ is benzyl, and R⁷ is as defined above in the Table 1A.

Table 1.16A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is N, A² is C—R², and R², R³, R⁴, and R⁸ are hydrogen, and R⁷is as defined above in the Table 1A.

Table 1.17A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is N, A² is C—R², and R², R³, and R⁴ are hydrogen, R⁸ ismethyl, and R⁷ is as defined above in the Table 1A.

Table 1.18A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is N, A² is C—R², and R², R³, and R⁴ are hydrogen, R⁸ is allyl,and R⁷ is as defined above in the Table 1A.

Table 1.19A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is N, A² is C—R², and R², R³, and R⁴ are hydrogen, R⁸ ispropargyl, and R⁷ is as defined above in the Table 1A.

Table 1.20A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 0, A¹ is N, A² is C—R², and R², R³, and R⁴ are hydrogen, R⁸ isbenzyl, and R⁷ is as defined above in the Table 1A.

Table 1.21A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², R⁴, and R⁸ are hydrogen, R³ isfluorine, and R⁷ is as defined above in the Table 1A.

Table 1.22A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², and R⁴ are hydrogen, R³ isfluorine, R⁸ is methyl, and R⁷ is as defined above in the Table 1A.

Table 1.23A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², and R⁴ are hydrogen, R³ isfluorine, R⁸ is allyl, and R⁷ is as defined above in the Table 1A.

Table 1.24A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², and R⁴ are hydrogen, R³ isfluorine, R⁸ is propargyl, and R⁷ is as defined above in the Table 1A.

Table 1.25A:

This table discloses 25 specific compounds of formula (T-1A) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², and R⁴ are hydrogen, R³ isfluorine, R⁸ is benzyl, and R⁷ is as defined above in the Table 1A.

Table 1.1B:

This table discloses 25 specific compounds of the formula (T-1B):

wherein n is 0, A¹ is C—R¹, A² is C—R², and R¹, R², R³, R⁴, and R⁸ arehydrogen, and R⁷ is as defined below in the Table 1B.

Each of Tables 1.2B to 1.10B (which follow Table 1B) make available 25individual compounds of the formula (T-1B) in which n, A¹, A², R¹, R²,R³, R⁴, R⁵, R⁶, and R⁸ are as specifically defined in Tables 1.2B to1.10B, which refer to Table 1B wherein R⁷ is specifically defined.

TABLE 1B Compound no. R⁷ 1B.001 H 1B.002 methyl 1B.003 ethyl 1B.004propyl 1B.005 isopropyl 1B.006 cyclopropyl 1B.007 butyl 1B.008 allyl1B.009 propargyl 1B.010 3,3-dichloroallyl 1B.011 2-hydroxyethyl 1B.0122-hydroxypropyl 1B.013 2-methoxyethyl 1B.014 2-difluoromethoxyethyl1B.015 2-methoxypropyl 1B.016 2-hydroxy-1-methyl-ethyl 1B.0172-methoxy-1-methyl-ethyl 1B.018 2-difluoromethoxy-1-methyl-ethyl 1B.019methyl 2-acetate 1B.020 methyl 2-propanoate 1B.0212-(tert-butylamino)-2-oxo-ethyl 1B.022 cyclopropylmethyl 1B.023 phenyl1B.024 benzyl 1B.025 2-furylmethylTable 1.2B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², R³, and R⁴ are hydrogen, R⁸ ismethyl, and R⁷ is as defined above in the Table 1B.

Table 1.3B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², R³, and R⁴ are hydrogen, R⁸ isallyl, and R⁷ is as defined above in the Table 1B.

Table 1.4B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², R³, and R⁴ are hydrogen, R⁸ ispropargyl, and R⁷ is as defined above in the Table 1B.

Table 1.5B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 0, A¹ is C—R¹, A² is C—R², and R¹, R², R³, and R⁴ are hydrogen, R⁸ isbenzyl, and R⁷ is as defined above in the Table 1B.

Table 1.6B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², R³, R⁴, R⁵, R⁶, and R⁸ arehydrogen, and R⁷ is as defined above in the Table 1B.

Table 1.7B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², R³, R⁴, R⁵, and R⁶ arehydrogen, R⁸ is methyl, and R⁷ is as defined above in the Table 1B.

Table 1.8B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², R³, R⁴, R⁵, and R⁶ arehydrogen, R⁸ is allyl, and R⁷ is as defined above in the Table 1B.

Table 1.9B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², R³, R⁴, R⁵, and R⁶ arehydrogen, R⁸ is propargyl, and R⁷ is as defined above in the Table 1B.

Table 1.10B:

This table discloses 25 specific compounds of formula (T-1B) wherein nis 1, A¹ is C—R¹, A² is C—R², and R¹, R², R³, R⁴, R⁵, and R⁶ arehydrogen, R⁸ is benzyl, and R⁷ is as defined above in the Table 1B.

EXAMPLES

The Examples which follow serve to illustrate the invention. Thecompounds of the invention can be distinguished from known compounds byvirtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppmor 0.2 ppm.

Compounds of Formula (I) may possess any number of benefits including,inter alia, advantageous levels of biological activity for protectingplants against diseases that are caused by fungi or superior propertiesfor use as agrochemical active ingredients (for example, greaterbiological activity, an advantageous spectrum of activity, an increasedsafety profile (including improved crop tolerance), improvedphysico-chemical properties, or increased biodegradability).

Throughout this description, LC/MS means Liquid Chromatography MassSpectrometry and the description of the apparatus and the method(Methods A, B and C) is as follows:

The Description of the LC/MS Apparatus and the Method A is:

SQ Detector 2 from Waters

Ionisation method: Electrospray

Polarity: positive and negative ions

Capillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone GasFlow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650

Mass range: 100 to 900 Da

DAD Wavelength range (nm): 210 to 500

Method Waters ACQUITY UPLC with the Following HPLC Gradient Conditions:

(Solvent A: Water/Methanol 20:1 + 0.05% formic acid and Solvent B:Acetonitrile + 0.05% formic acid) Time (minutes) A (%) B (%) Flow rate(ml/min) 0 100 0 0.85 1.2 0 100 0.85 1.5 0 100 0.85Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.The Description of the LC/MS Apparatus and the Method B is:SQ Detector 2 from WatersIonisation method: ElectrosprayPolarity: positive ionsCapillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 400, Cone GasFlow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700Mass range: 140 to 800 DaDAD Wavelength range (nm): 210 to 400Method Waters ACQUITY UPLC with the Following HPLC Gradient Conditions

(Solvent A: Water/Methanol 9:1 + 0.1% formic acid and Solvent B:Acetonitrile + 0.1% formic acid) Time (minutes) A (%) B (%) Flow rate(ml/min) 0 100 0 0.75 2.5 0 100 0.75 2.8 0 100 0.75 3.0 100 0 0.75Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.The Description of the LC/MS Apparatus and the Method C is:SQ Detector 2 from WatersIonisation method: ElectrosprayACQUITY H Class UPLC, Mass Spectrometer from WatersPolarity: positive and Negative Polarity SwitchScan Type MS1 ScanCapillary (kV) 3.00, Cone (V) 40.00, Desolvation Temperature (° C.) 500,Cone Gas Flow (L/Hr) 50,Desolvation Gas Flow (L/Hr) 1000Mass range: 0 to 2000 DaDAD Wavelength range (nm): 200 to 350Method Waters ACQUITY UPLC with the Following HPLC Gradient Conditions

(Solvent A: Water + 0.1% formic acid and Solvent B: Acetonitrile) Time(minutes) A (%) B (%) Flow rate (ml/min) 0 70 30 0.5 0.05 70 30 0.5 0.85 95 0.5 1.8 5 95 0.5 2.45 70 30 0.5 2.50 70 30 0.5Type of column: Waters ACQUITY UPLC BEH C18; Column length: 50 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.7 micron;Temperature: 35° C.

Where necessary, enantiomerically pure final compounds may be obtainedfrom racemic materials as appropriate via standard physical separationtechniques, such as reverse phase chiral chromatography, or throughstereoselective synthetic techniques, e.g., by using chiral startingmaterials.

FORMULATION EXAMPLES

Wettable Powders

a) b) c) active ingredient [compound of 25%  50% 75% Formula (IA) or(IB)] sodium lignosulfonate 5%  5% — sodium lauryl sulfate 3% —  5%sodium diisobutylnaphthalenesulfonate —  6% 10% phenol polyethyleneglycol ether —  2% — (7-8 mol of ethylene oxide) highly dispersedsilicic acid 5% 10% 10% Kaolin 62%  27% —

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders that can be diluted with water to give suspensions of thedesired concentration.

Powders for Dry Seed Treatment

a) b) c) active ingredient [compound of 25% 50% 75% Formula (IA) or(IB)] light mineral oil  5%  5%  5% highly dispersed silicic acid  5% 5% — Kaolin 65% 40% — Talcum — 20%

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording powders thatcan be used directly for seed treatment.

Emulsifiable Concentrate

active ingredient [compound of Formula (IA) or (IB)] 10%  octylphenolpolyethylene glycol ether 3% (4-5 mol of ethylene oxide) calciumdodecylbenzenesulfonate 3% castor oil polyglycol ether (35 mol ofethylene oxide) 4% Cyclohexanone 30% 

Emulsions of any required dilution, which can be used in plantprotection, can be obtained from this concentrate by dilution withwater.

Dusts

a) b) c) Active ingredient [compound of  5%  6%  4% Formula (IA) or(IB)] Talcum 95% — — Kaolin — 94% — mineral filler — — 96%

Ready-for-use dusts are obtained by mixing the active ingredient withthe carrier and grinding the mixture in a suitable mill. Such powderscan also be used for dry dressings for seed.

Extruder Granules

Active ingredient [compound of 15% Formula (IA) or (IB)] sodiumlignosulfonate  2% Carboxymethylcellulose  1% Kaolin 82%

The active ingredient is mixed and ground with the adjuvants, and themixture is moistened with water. The mixture is extruded and then driedin a stream of air.

Coated Granules

Active ingredient [compound of 8% Formula (IA) or (IB)] polyethyleneglycol (mol. wt. 200) 3% Kaolin 89% 

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coated granulesare obtained in this manner.

Suspension Concentrate

active ingredient [compound of Formula (IA) or (IB)] 40% propyleneglycol 10% nonylphenol polyethylene glycol ether (15 mol of ethyleneoxide)  6% Sodium lignosulfonate 10% Carboxymethylcellulose  1% siliconeoil (in the form of a 75% emulsion in water)  1% Water 32%

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Flowable Concentrate for Seed Treatment

active ingredient [compound of Formula (IA) or (IB)] 40%  propyleneglycol 5% copolymer butanol PO/EO 2% tristyrenephenole with 10-20 molesEO 2% 1,2-benzisothiazolin-3-one (in the form of a 20% solution 0.5%  inwater) monoazo-pigment calcium salt 5% Silicone oil (in the form of a75% emulsion in water) 0.2%  Water 45.3%  

The finely ground active ingredient is intimately mixed with theadjuvants, giving a flowable concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Slow-Release Capsule Suspension

28 parts of a combination of the compound of Formula (IA) or (IB) aremixed with 2 parts of an aromatic solvent and 7 parts of toluenediisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). Thismixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol,0.05 parts of a defoamer and 51.6 parts of water until the desiredparticle size is achieved. To this emulsion a mixture of 2.8 parts1,6-diaminohexane in 5.3 parts of water is added. The mixture isagitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of athickener and 3 parts of a dispersing agent. The capsule suspensionformulation contains 28% of the active ingredients. The medium capsulediameter is 8-15 microns.

The resulting formulation is applied to seeds as an aqueous suspensionin an apparatus suitable for that purpose.

List of Abbreviations

-   ° C.=degrees Celsius-   CDCl₃=chloroform-d-   DMSO=dimethyl sulfoxide-   d=doublet-   EtOAc=ethyl acetate-   HCl=hydrochloric acid-   m=multiplet-   MHz=mega hertz-   mp=melting point-   NBS=N-bromosuccinimide-   ppm=parts per million-   s=singlet-   t=triplet-   TFAA=trifluoroacetic acid anhydride-   THF=tetrahydrofuran-   LC/MS=Liquid Chromatography Mass Spectrometry (description of the    apparatus and the methods used for LC/MS analysis are given above)

PREPARATION EXAMPLES Example 1: This Example Illustrates the Preparation2-fluoro-N-methoxy-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(Compound 1.1 of Table T1)

Step 1: Preparation of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic Acid

A solution of hydroxyamine hydrochloride (3.0 g) in water (20 mL) wasadded at room temperature to a stirred solution of4-cyano-2-fluorobenzoic acid (3.52 g, 21.3 mmol) in ethanol (35 mL),followed by dropwise addition of potassium carbonate (1.60 g). Then8-hydroxyquinoline (0.041 g, 0.28 mmol) was added. The resulting thicksuspension was heated to reflux for 3 hours to obtain a yellow solution.After removal of ethanol, under reduced pressure, the residue wasacidified with 2N HCl to pH 3. The white precipitate was filtered,washed with water and dried under reduced pressure at 50° C. to yield2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid as beige solid.mp: >250° C.

¹H NMR (400 MHz, DMSO-d6) δ ppm: 13.22 (s, 1H), 10.00 (s, 1H), 7.85 (t,1H), 7.63 (m, 1H), 7.54-7.61 (m, 1H).

Step 2: Preparation of2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic Acid

Trifluoroacetic anhydride (4.1 mL) was added dropwise to a stirredsuspension of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid (3.80 g,19.0 mmol) in THF (77 mL) at 10 to 15° C. The beige suspension waswarmed to room temperature and stirred overnight. After evaporation, thecrude product was stirred with heptane/ethylacetate (95:5), filtered anddried under reduced pressure at 50° C. to yield2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid asyellow solid. mp: 175-177° C.

¹H NMR (400 MHz, DMSO-d₆) δ ppm: 13.55 (s, 1H), 8.12 (t, 1H), 8.00 (d,1H), 7.94 (d, 1H).

Step 3: Preparation of2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl Chloride

To a white suspension of2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (3.6g, 13.0 mmol) and CH₂Cl₂ (130 mL) at room temperature was added thionylchloride (1.51 mL) dropwise. The resulting suspension was heated toreflux and stirred for 3 hours, to obtain a yellow solution. The solventwas evaporated under reduced pressure at 30° C. to yield2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl chlorideas yellowish solid that was used directly without purification.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.26 (t, 1H), 8.07 (m, 1H), 7.99 (m, 1H).

Step 4: Preparation of2-fluoro-N-(2-oxooxazolidin-3-yl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide

To a screw-cap vial containing2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl chloride(0.13 g, 0.44 mmol) suspended in CH₂Cl₂ (10 mL) cooled to 0° C. wasadded methoxyamine hydrochloride (37 mg, 0.44 mmol) dissolved in CH₂Cl₂(1 mL) then triethylamine (0.14 mL) was introduced dropwise. Afterstirring for 4 hours, the volatile reaction components were removedunder reduced pressure and the crude residue was purified by flashchromatography over silica gel (heptane/ethyl acetate gradient) to givethe title compound as a white solid (mp: 122-125° C.). LC/MS retentiontime=0.88 minutes, 306 (M+H).

¹H NMR (400 MHz, CDCl₃): δ 9.27 (d, 1H), 8.29 (m, 1H), 8.07 (dd, 1H),7.96 (dd, 1H), 3.94 (s, 3H).

Example 2: this Example Illustrates the Preparation ofN-(cyclopropylmethyl)-2-fluoro-N-methoxy-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(Compound 1.8 of Table T1)

To a screw-cap vial containing2-fluoro-N-(2-oxooxazolidin-3-yl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(0.07 g, 0.24 mmol) dissolved in acetone (10 mL) was added potassiumcarbonate (0.08 g, 0.58 mmol) and bromomethyl cyclopropane (0.03 mL,0.26 mmol). After stirring overnight, bromomethyl cyclopropane (0.03 mL,0.26 mmol) was re-introduced and the reaction was stirred for 24 hours.Upon completion, volatiles were removed under reduced pressure and thecrude contents were poured into a separating funnel containing EtOAc andwater. The organic layer was separated, washed with brine and dried overNa₂SO₄. The solvent was removed under reduced pressure and the cruderesidue was purified by flash chromatography over silica gel(heptane/ethyl acetate gradient) to give the title compound as a yellowoil (35 mg, 41% yield). LC/MS retention time=1.10 minutes, 360 (M+H).

¹H NMR (400 MHz, CDCl₃): δ 7.96 (d, 1H), 7.89 (d, 1H), 7.71 (t, 1H),3.95 (s, 3H), 1.23 (m, 3H), 0.61 (m, 2H), 0.26 (m, 2H).

Example 3: Preparation ofN-allyloxy-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide(Compound 2.14 of Table 2)

Step 1: Preparation of N′-hydroxy-4-methyl-benzamidine

To a stirring suspension of 4-methylbenzonitrile (35 g, 0.29 mol) inethanol (220 mL) and water (440 mL) was added at room temperaturehydroxylamine hydrochloride (41.1 g, 0.58 mol), potassium carbonate(65.4 g, 0.47 mol) and 8-hydroxyquinoline (0.22 g, 1.5 mmol). Thereaction mixture was heated at 80° C. for 4 hours. The mixture wascooled to room temperature and diluted with 2N HCl until pH 8. Ethanolwas evaporated under reduced pressure then the mixture was filtered,washed with water, and dried under vacuum to afford 39.1 g ofN′-hydroxy-4-methyl-benzamidine which was used without furtherpurification. LC/MS (Method A) retention time=0.23 minutes, 151.0 (M+H).

Step 2: Preparation of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

To a stirring solution of N′-hydroxy-4-methyl-benzamidine (38.7 g, 0.25mol) in 2-methyltetrahydrofuran (750 mL) was added TFAA at 0° C. Thereaction mixture was stirred at 15° C. for two hours then diluted withwater. The organic layer was separated, washed successively with anaqueous sodium bicarbonate solution, aqueous ammonium chloride solution,and water. The organic phase was then dried over sodium sulfate,filtered and evaporated to dryness. The crude material was subjected toflash chromatography over silica gel (eluent heptane/EtOAc 99:1 to90:10) to afford 54.1 g of3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole as clear oil, whichsolidified after storage. LC/MS (Method A) retention time=1.15 minutes,mass not detected.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.41 (s).

Step 3a: Preparation of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

A stirring mixture of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole(56.0 g, 0.24 mol) and NBS (45.4 g, 0.25 mol) in tetrachloromethane (480mL) under argon was heated to 70° C. AIBN (4.03 g, 24 mmol) was addedand the reaction mixture was stirred at 65° C. for 18 hours. The mixturewas cooled to 25° C. and diluted with dichloromethane and water. Theorganic layer was washed with sodium bicarbonate solution, dried oversodium sulfate, filtered and evaporated to dryness. The crude materialwas subjected to flash chromatography over silica gel (eluentcyclohexane/EtOAc 100:0 to 95:5) to afford 44.7 g of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole as awhite solid mp: 58-63° C.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.32 (s).

3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (seebelow) was isolated as by-product as white solid (mp 61-66° C.).

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.34 (s).

Step 3b: Preparation of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

To a stirring 1:9 ratio mixture of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole and3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (10.2g) in acetonitrile (95 mL), water (1.9 mL) and DIPEA (6.20 mL, 35.7mmol), was added diethylphosphite (4.7 mL, 35.7 mmol) at 5° C. Themixture was stirred at 5-10° C. for two hours, water and 1M HCl wereadded, and acetonitrile was evaporated under reduced pressure. The whiteslurry was extracted with dichloromethane and the combined organiclayers were dried over sodium sulfate, and filtered. The solvent wasremoved under reduced pressure and the resultant crude material wassubjected to flash chromatography over silica gel (eluentcyclohexane/EtOAc 99:1 to 9:1) to afford 7.10 g of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole.

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.32 (s).

Step 4: Preparation of2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetonitrile

To a solution of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (10.0 g,32.6 mmol) and trimethylsilylformonitrile (4.2 g, 43.9 mmol) inacetonitrile (400 mL) at 0° C. was added a 1M THF solution oftetrabutylammonium hydrofluoride (42.3 mL, 42.3 mmol). The reaction wasstirred for 3 hours while reaching room temperature then the reactioncontents were diluted with water and extracted with ethyl acetate. Thecombined organic layer organic was washed with water, brine, dried overNa₂SO₄, and concentrated under reduced pressure. The resultant crudematerial was subjected to flash chromatography over silica gel (eluentcyclohexane/EtOAc 8:2) to afford2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetonitrile (7.0g, 82% yield).

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.15 (m, 2H), 7.55 (m, 2H), 3.88 (m, 2H).

Step 5: Preparation of methyl2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetate

To a solution of2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetonitrile (7.0g, 27.6 mmol) in methanol (70 mL) was added chloro(trimethyl)silane(18.0 g, 165.9 mmol) at room temperature then the reaction was heated at65° C. for 12 hours. After the contents were cooled to room temperaturemethanol was removed under reduced pressure and the resultant residuewas diluted with water and extracted with ethyl acetate. The organiclayer organic was washed with a saturated aqueous NaHCO₃ solution,brine, dried over Na₂SO₄, and concentrated under reduced pressure. Theresultant crude material was subjected to flash chromatography oversilica gel (eluent cyclohexane/EtOAc 99:1 to 9:1) to afford methyl2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetate (6.5 g, 23mmol, 71% yield).

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.11 (d, 2H), 7.48 (d, 2H), 3.75 (s, 2H),3.74 (s, 3H).

Step 6: Preparation of2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetic Acid

To a solution of methyl2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetate (2.90 g,10.1 mmol) in methanol (116 mL) was added dihydroxybarium octahydrate(6.39 g, 20.3 mmol) at 0° C. and the reaction was stirred for 1 hourwhile reaching room temperature. The reaction contents were then dilutedwith water and washed with ethyl acetate. The aqueous layer wasacidified to pH 2 using a 1M HCl aqueous solution and extracted withethyl acetate. The combined organic layer organic was washed with water,brine, dried over Na₂SO₄, and concentrated under reduced pressure. Theresultant crude material was subjected to flash chromatography oversilica gel (eluent cyclohexane/EtOAc 8:2) to afford2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetic acid (2.6g, 94% yield).

¹H NMR (400 MHz, CDCl₃) δ ppm: 12.49 (brs, 1H), 8.02 (d, 2H), 7.53 (d,2H), 3.72 (s, 2H).

Step 7: Preparation ofN-allyloxy-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide

A 10 mL vial was charged with O-allylhydroxylamine hydrochloride (0.091g, 0.83 mmol), N,N-dimethylformamide (2.5 mL) and DIPEA (0.214 g, 1.65mmol) then stirred at for 30 minutes.2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetic acid (0.15g, 0.55 mmol) was added followed by HATU (0.314 g, 0.83 mmol) and thereaction was stirred 1 h. The reaction solution was diluted with water 5and ethyl acetate then extracted with ethyl acetate. The combinedorganic layer was washed with water, dried over Na₂SO₄, and concentratedunder reduced pressure. The resultant crude material was subjected toflash chromatography over silica gel (eluent cyclohexane/EtOAc 99:1 to9:1) to affordN-allyloxy-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide(0.11 g, 59% yield) as a white solid. mp 153-158° C.; LC/MS retentiontime=0.95 minutes, 328.2 (M+H).

¹H NMR (400 MHz, CDCl₃) δ ppm: 8.10 (d, 2H), 7.95 (brs, 1H), 7.46 (d,2H), 5.93 (m, 1H), 5.32 (m, 2H), 4.38 (m, 2H), 3.80 (m, 1H), 3.57 (m,1H).

¹⁹F NMR (400 MHz, CDCl₃) δ ppm: −65.66 (s).

TABLE T1 Melting point (mp) data and/or retention times (RT) forcompounds according to Formula (IA): Compound RT [M + H] mp Entry NameStructure (min) (measured) Method (° C.) 1.1 2-fluoro-N- methoxy-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

122- 125 1.2 2-fluoro-N- methoxy-N- methyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

0.98 320 A 1.3 2-fluoro-N- methoxy-N-[(2,4,6- trichlorophenyl)methyl]-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.27 500 A 1.4 2-fluoro-N- methoxy-N-[1- methyl-2-(2,4,6-trichlorophenyl) ethyl]-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide

83.5- 86.2 1.5 methyl 4-[[2-fluoro- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzoyl]- hydroxy-amino]-1- methoxy- piperidine-4-carboxylate

1.77 463 B 1.6 N-benzyl-2-fluoro- N-methoxy-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.14 396 A 1.7 2-fluoro-N-(2- furylmethyl)-N- methoxy-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.08 386 A 1.8 N- (cyclopropylmethyl)- 2-fluoro-N- methoxy-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.1 360 A 1.9 2-fluoro-N- methoxy-N-(1- methyl-2- tetrahydropyran-2-yloxy-ethyl)-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.15 447 A 1.10 2-fluoro-N- methoxy-N-prop-2- ynyl-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.02 344 A 1.11 N-(2-cyano-1- methyl-ethoxy)-2- fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

85.8- 88 1.12 2-fluoro-N-(2- hydroxy-1-methyl- ethyl)-N-methoxy- 4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.09 364 A 1.13 N-ethoxy-3-fluoro- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

139- 144 1.14 N-(2,2- difluoroethoxy)-3- fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

138- 140 1.15 N-allyloxy-3-fluoro- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

132- 136 1.16 N-benzyloxy-3- fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

178- 181 1.17 2-[3-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]-N- methoxy- acetamide

131- 133 1.18 2-[3-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]-N- methoxy-N- methyl-acetamide

1.52 334 C 1.19 2-[2-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]-N- methoxy-N- methyl-acetamide

104- 106 1.20 2-[2-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]-N- methoxy- acetamide

150- 152 1.21 N-ethoxy-2-[2- fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]acetamide

81- 83 1.22 N-ethoxy-2-[3- fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]acetamide

150- 152 1.23 N-(2,2- difluoroethoxy)-2- [2-fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]acetamide

114- 116 1.24 2-[3-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]-N- methoxy-N-(1- phenylethyl) acetamide

1.63 424 C 1.25 N-(1- cyclopropylethyl)- 2-[3-fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]-N- methoxy- acetamide

1.60 388 C 1.26 [2-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]- isoxazolidin-2-yl- methanone

60.3- 62.4 1.27 [2-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]- (oxazinan-2- yl)methanone

57.3- 59.4

TABLE T2 Melting point (mp) data and/or retention times (RT) forcompounds according to Formula (IB): Compound RT [M + H] mp Entry NameStructure (min) (measured) Method (° C.) 2.1 methyl 4-[hydroxy- [4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzoyl]amino]-1-methoxy-piperidine- 4-carboxylate

1.77 445.2 B 2.2 N-[2-(tert- butylamino)-2-oxo- ethyl]-N-methoxy-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.59 401 B 2.3 methyl (2S)-2- [methoxy-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzoyl]amino] propanoate

1.63 374 B 2.4 4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzenecarbo- hydroxamic acid

175- 177   2.5 N-benzyl-N- methoxy-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.12 378 A 2.6 N-methoxy-N-prop- 2-ynyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.01 326 A 2.7 N-(3,3-dichloroallyl)- N-methoxy-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.16 396 A 2.8 methyl 2-[methoxy- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzoyl]amino] acetate

0.99 360 A 2.9 methyl 2-[methoxy- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzoyl]amino] propanoate

1.04 374 A 2.10 N-allyl-N-methoxy- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.05 328 A 2.11 N-prop-2-ynoxy-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

167- 169   2.12 N-allyloxy-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide

134- 135   2.13 N-methoxy-2-[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]acetamide

131- 138   2.14 N-allyloxy-2-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]acetamide

153- 158   2.15 N-benzyloxy-2-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]acetamide

135- 138   2.16 N-ethoxy-2-[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]acetamide

171- 183   2.17 N-(2,2- difluoroethoxy)-2-[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]acetamide

140- 146   2.18 N-(2,2- difluoroethoxy)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

134- 137   2.19 N-methoxy-N- (oxetan-3-yl)-2-[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]acetamide

1.47 358 C 2.20 N-methoxy-N-(1- phenylethyl)-2-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]acetamide

1.64 405.9 C 2.21 N-(1- cyclopropylethyl)-N- methoxy-2-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]acetamide

1.63 370 C 2.22 N- (cyclopropylmethyl)- N-methoxy-2-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]acetamide

1.57 356 C 2.23 2-oxa-3- azabicyclo[2.2.2]oct- 5-en-3-yl-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methanone

 89-  93 2.24 2-oxa-3- azabicyclo[2.2.2] octan-3-yl-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methanone

120- 121   2.25 N-[(2- cyclopropylcyclo- propyl)methyl]-N-methoxy-2-[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]acetamide

1.58 396 C 2.26 N-[(2- cyclopropylcyclo- propyl)methyl]-N-hydroxy-2-[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]acetamide

1.58 381 C

BIOLOGICAL EXAMPLES General Examples of Leaf Disk Tests in Well Plates

Leaf disks or leaf segments of various plant species are cut from plantsgrown in a greenhouse. The cut leaf disks or segments are placed inmultiwell plates (24-well format) onto water agar. The leaf disks aresprayed with a test solution before (preventative) or after (curative)inoculation. Compounds to be tested are prepared as DMSO solutions (max.10 mg/ml) which are diluted to the appropriate concentration with 0.025%Tween20 just before spraying. The inoculated leaf disks or segments areincubated under defined conditions (temperature, relative humidity,light, etc.) according to the respective test system. A singleevaluation of disease level is carried out 3 to 14 days afterinoculation, depending on the pathosystem. Percent disease controlrelative to the untreated check leaf disks or segments is thencalculated.

General Examples of Liquid Culture Tests in Well Plates

Mycelia fragments or conidia suspensions of a fungus prepared eitherfreshly from liquid cultures of the fungus or from cryogenic storage,are directly mixed into nutrient broth. DMSO solutions of the testcompound (max. 10 mg/ml) are diluted with 0.025% Tween20 by a factor of50 and 10 μl of this solution is pipetted into a microtiter plate(96-well format). The nutrient broth containing the fungalspores/mycelia fragments is then added to give an end concentration ofthe tested compound. The test plates are incubated in the dark at 24° C.and 96% relative humidity. The inhibition of fungal growth is determinedphotometrically after 2 to 7 days, depending on the pathosystem, andpercent antifungal activity relative to the untreated check iscalculated.

Example 1: Fungicidal Activity Against Puccinia recondita f. Sp.tritici/Wheat/Leaf Disc Preventative (Brown Rust)

Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf disks are inoculated with a spore suspension of thefungus 1 day after application. The inoculated leaf segments areincubated at 19° C. and 75% rh under a light regime of 12 h light/12 hdarkness in a climate cabinet and the activity of a compound is assessedas percent disease control compared to untreated when an appropriatelevel of disease damage appears in untreated check leaf segments (7-9days after application).

The following compounds gave at least 80% control of Puccinia reconditaf. sp. tritici at 200 ppm when compared to untreated control under thesame conditions, which showed extensive disease development:

Compounds (from Table T1) 1.1, 1.2, 1.5, 1.6, 1.7, 1.8, 1.10, 1.11,1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.21, 1.22, 1.23, 1.24,1.26, and 1.27.

Compounds (from Table T2) 2.1, 2.2, 2.4, 2.5, 2.6, 2.7, 2.8, 2.10, 2.11,2.12, 2.13, 2.14, 2.15, 2.16, 2.17, 2.18, 2.19, 2.23, and 2.26.

Example 2: Fungicidal Activity Against Puccinia recondita f. Sp.tritici/Wheat/Leaf Disc Curative (Brown Rust)

Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates(24-well format). The leaf segments are inoculated with a sporesuspension of the fungus. Plates are stored in darkness at 19° C. and75% rh. The formulated test compound diluted in water is applied 1 dayafter inoculation. The leaf segments are incubated at 19° C. and 75% rhunder a light regime of 12 h light/12 h darkness in a climate cabinetand the activity of a compound is assessed as percent disease controlcompared to untreated when an appropriate level of disease damageappears in untreated check leaf segments (6-8 days after application).

The following compounds gave at least 80% control of Puccinia reconditaf. sp. tritici at 200 ppm when compared to untreated control under thesame conditions, which showed extensive disease development:

Compounds (from Table T1) 1.1, 1.2, 1.5, 1.6, 1.7, 1.8, 1.10, 1.11,1.12, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.21, 1.22, 1.23, 1.25,1.26, and 1.27.

Compounds (from Table T2) 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 2.10,2.11, 2.12, 2.13, 2.16, 2.17, 2.18, 2.19, 2.22, 2.23, 2.24, and 2.26.

Example 3: Fungicidal Activity Against Phakopsorapachyrhizi/Soybean/Leaf Disc Preventative (Asian Soybean Rust)

Soybean leaf disks are placed on water agar in multiwell plates (24-wellformat) and sprayed with the formulated test compound diluted in water.One day after application leaf discs are inoculated by spraying a sporesuspension on the lower leaf surface. After an incubation period in aclimate cabinet of 24-36 hours in darkness at 20° C. and 75% rh leafdisc are kept at 20° C. with 12 h light/12 h darkness and 75% rh. Theactivity of a compound is assessed as percent disease control comparedto untreated when an appropriate level of disease damage appears inuntreated check leaf disks (12-14 days after application).

The following compounds gave at least 80% control of Phakopsorapachyrhizi at 200 ppm when compared to untreated control under the sameconditions, which showed extensive disease development:

Compounds (from Table T1) 1.1, 1.2, 1.5, 1.6, 1.7, 1.8, 1.10, 1.11,1.16, 1.17, 1.18, 1.19, 1.22, and 1.27.

Compounds (from Table T2) 2.1, 2.2, 2.4, 2.5, 2.6, 2.7, 2.8, 2.10, 2.11,2.12, 2.13, 2.16, 2.17, 2.22, 2.23, and 2.24.

Example 4: Fungicidal Activity Against Glomerella lagenarium(Colletotrichum lagenarium) Liquid Culture/Cucumber/Preventative(Anthracnose)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is measuredphotometrically 3-4 days after application.

The following compounds gave at least 80% control of Glomerellalagenarium at 20 ppm when compared to untreated control under the sameconditions, which showed extensive disease development:

Compounds (from Table T1) 1.1, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11,1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.21, 1.22, 1.23,1.24, 1.25, 1.26, and 1.27.

Compounds (from Table T2) 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9,2.10, 2.11, 2.12, 2.13, 2.14, 2.15, 2.16, 2.17, 2.18, 2.19, 2.20, 2.21,2.22, 2.23, 2.24, 2.25, and 2.26.

Example 5: Fungicidal Activity Against Uromyces viciae-Fabae/FieldBean/Leaf Disc Preventative (Faba-Bean Rust)

Field bean leaf discs are placed on water agar in multiwell plates(96-well format) and 10 μl of the formulated test compound diluted inacetone and a spreader pipetted onto the leaf disc. Two hours afterapplication leaf discs are inoculated by spraying a spore suspension onthe lower leaf surface. The leaf discs are incubated in a climatecabinet at 22° C. with 18 hour day and 70% relative humidity. Theactivity of a compound is assessed as percent disease control comparedto untreated when an appropriate level of disease damage appears inuntreated check leaf disks (12 days after application).

The following compounds at 100 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf discs under the same conditions, which show extensivedisease development.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9,1.10, 1.11, 1.12, 1.26, and 1.27.

Compounds (from Table T2) 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9,2.10, 2.11, 2.12, 2.23, and 2.24.

The invention claimed is:
 1. A compound of Formula (IA):

wherein A¹ is CR¹ and R¹ is halogen, A² is CR² and R² is hydrogen, and R³ and R⁴ are hydrogen; or A¹ is CR¹ and R¹ is hydrogen, A² is CR² and R² is hydrogen; R³ is halogen, and R⁴ is hydrogen; n=0 or 1; R⁵ and R⁶ independently represent hydrogen or methyl; R⁷ resents hydrogen, C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄haloalkyl, C₃-₆haloalkenyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, C₁-₄haloalkoxyC₁-₆alkyl, C₁-₄alkylcarbonylC₁-₄alkyl, C₁-₄alkoxycarbonylC₁-₄alkyl, C₁-₄alkylaminocarbonylC₁-₄alkyl, di-C₁-₄alkylaminocarbonylC₁-₄alkyl, C₃-₈cycloalkyl, C₃-₈cycloalkylC₁-₃alkyl, phenyl, phenylC₁-₃alkyl, heteroaryl, heteroarylC₁-₃alkyl, wherein the heteroaryl moiety of said heteroaryl and heteroarylC₁-₃alkyl is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC₁-₃alkyl or heterocyclyloxyC₁-3alkyl, wherein the heterocyclyl moiety of said heterocyclyl, heterocyclylC₁-₃alkyl and heterocyclyloxyC₁-₃alkyl is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein any of cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2, 3 or 4 substituents, which may be the same or different, selected from R⁹; R⁸ represents hydrogen, C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄haloalkyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, phenyl or phenylC₁-₃alkyl; R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C₁-₄alkoxycarbonyl, C₁-₄alkylaminocarbonyl, di-C₁-₄alkylaminocarbonyl, or cyclopropyl; or R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N and NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N and NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl; or a salt or an N-oxide thereof; or a compound of Formula (TB):

wherein A¹ is CR¹, wherein R¹ is hydrogen; A² is CR², wherein R² is hydrogen; R³ and R⁴ both represent hydrogen; n=0 or 1; R⁵ and R⁶ independently represent hydrogen or methyl; R⁷ represents hydrogen, C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄haloalkyl, C₃-₆haloalkenyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, C₁-₄haloalkoxyC₁-₆alkyl, C₁-₄alkylcarbonylC₁-₄alkyl, C₁-₄alkoxycarbonylC₁-₄alkyl, C₁-₄alkylaminocarbonylC₁-₄alkyl, di-C₁-₄alkylaminocarbonylC₁-₄alkyl, C₃-₈scycloalkyl, C₃-₈cycloalkylC₁-₃alkyl, phenyl, phenylC₁-₃alkyl, heteroaryl, heteroarylC₁-₃alkyl, wherein the heteroaryl moiety of said heteroaryl and heteroarylC₁-₃alkyl is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC₁-₃alkyl or heterocyclyloxyC₁-3alkyl, wherein the heterocyclyl moiety of said heterocyclyl, heterocyclylC₁-₃alkyl and heterocyclyloxyCi-₃alkyl is a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein any of said cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2, 3 or 4 substituents, which may be the same or different, selected from R⁹; R⁸ represents C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄haloalkyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, phenyl, or phenylC₁-₃alkyl; R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C₁-₄alkoxycarbonyl, C₁-₄alkylaminocarbonyl, di-C₁-₄alkylaminocarbonyl, or cyclopropyl; or R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N and NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N and NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl; or a salt or an N-oxide thereof; with the proviso that the compound of Formula (IB) is not: N-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; N-methoxy-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; N-benzyloxy-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; N-methoxy-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide; or N-methoxy-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide.
 2. The compound of Formula (IA) according to claim 1, wherein R⁷ is selected from hydrogen, C₁-₆alkyl, C₁-₄haloalkyl, C₃-₆alkynyl, hydroxyC₁-₆alkyl, C₃-₈cycloalkyl, C₃-₈cycloalkylC₁-₃alkyl, phenyl, phenylC₁-₃alkyl, heteroaryl, heteroarylC₁-₃alkyl, heterocyclyl, heterocyclylC₁-₃alkyl and heterocyclyloxyC₁-₃alkyl, wherein any of said cycloalkyl, phenyl and heterocyclyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R⁹.
 3. The compound of Formula (IA) according to claim 1, wherein R⁸ is selected from hydrogen, C₁-₄alkyl, C₃-₆alkenyl, cyanoC₁-₆alkyl, phenyl and phenylC₁-₃alkyl.
 4. The compound of Formula (IA) according to claim 1, wherein R⁷ is selected from hydrogen, C₁-₄alkyl, C₃-₄alkynyl, C₁-₂haloalkyl, hydroxyC₁-₄alkyl, C₃-₆cycloalkyl, C₃-₆cycloalkylC₁-₃alkyl, phenyl, phenylC₁-₃alkyl, furanyl, furanylC₁-₃alkyl, piperidinyl, piperidinylC₁-₃alkyl and tetrahydropyranyloxyC₁-₃alkyl, wherein any of said cycloalkyl, phenyl, furanyl, piperidinyl and tetrahydropyranyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R⁹; and R⁸ is selected from hydrogen, methyl, ethyl, prop-1-enyl, 1-methyl-2-cyano-ethyl or benzyl.
 5. The compound of Formula (IA) according to claim 1, wherein: A¹ is CR¹and R¹ is fluoro, A² is CR² and R² is hydrogen, and R³ and R⁴ are hydrogen; or A¹ is CR¹ and R¹ is hydrogen, A² is CR² and R² is hydrogen; R³ is fluoro, and R⁴ is hydrogen.
 6. The compound of Formula (TB) according to claim 1, wherein R¹ is selected from hydrogen, C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄haloalkyl, C₃-₆haloalkenyl, C₁-₄alkoxycarbonylC₁-₄alkyl, C₁-₄alkylaminocarbonylC₁-₄alkyl, phenyl, phenylC₁-₃alkyl, heterocyclyl and heterocyclylC₁-₃alkyl, wherein any of said phenyl and heterocyclyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R⁹.
 7. The compound of formula (IB) according to claim 1, wherein R⁷ is C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄ha1oalkyl, C₃-₆haloalkenyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, C₁-₄haloalkoxyC₁-₆alkyl, C₁-₄alkylcarbonylC₁-₄alkyl, C₁-₄alkoxycarbonylC₁-₄alkyl, C₁-₄alkylaminocarbonylC₁-₄alkyl, di-C₁-₄alkylaminocarbonylC₁-₄alkyl, C3-8cycloalkyl, C₃-₈cycloalkylC₁-₃alkyl, phenyl, phenylC₁-₃ alkyl, heteroaryl, heteroarylC₁-₃ alkyl, wherein the heteroaryl moiety of said heteroaryl and heteroarylC₁-₃alkyl is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC₁-₃alkyl or heterocyclyloxyC1-3 alkyl, wherein the heterocyclyl moiety of said heterocyclyl, heterocyclylC₁-₃alkyl and heterocyclyloxyC₁-₃alkyl is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein any of cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2, 3 or 4 substituents, which may be the same or different, selected from R⁹.
 8. The compound of Formula (TB) according to claim 1, wherein R⁸ is selected from C₁-₄alkyl, C₃-₆alkenyl, C₃-₆alkynyl, phenyl and phenylC₁-₃alkyl.
 9. The compound of Formula (TB) according to claim 1, wherein R¹ is selected from hydrogen, C₁-₄alkyl, C3-4alkenyl, C3-4alkynyl, C₁-₄haloalkyl, C₃-₄haloalkenyl, C₁-₄alkoxycarbonylC₁-₄alkyl, C₁-₄alkylaminocarbonylC₁-₄alkyl, phenyl, phenylC₁-₃alkyl, piperidinyl and piperidinylC₁-₃alkyl wherein any of said phenyl and piperidinyl moieties is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R⁹; and R⁸ is selected from hydrogen, methyl, ethyl, prop-1-enyl, prop-1-ynyl, and benzyl.
 10. The compound according to claim 1, wherein n is
 0. 11. The compound of formula (IA) or formula (IB) according to claim 1, wherein: R⁸ represents C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄haloalkyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, phenyl or phenylC₁-₃alkyl.
 12. The compound of formula (IA) or formula (IB) according to claim 11, wherein n is
 0. 13. The compound of formula (IA) or formula (IB) according to claim 1, wherein R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N and NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl.
 14. The compound of formula (IA) according to claim
 1. 15. The compound of formula (TB) according to claim
 1. 16. The compound according to claim 1, wherein R⁵ and R⁶ are both hydrogen.
 17. The compound according to claim 1, wherein R⁹ is independently selected from halogen, methoxy and C₁-₄alkoxycarbonyl.
 18. An agrochemical composition comprising a fungicidally effective amount of a compound according to claim
 1. 19. The agrochemical composition according to claim 18, further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.
 20. A method of controlling or preventing infestation of plants by phytopathogenic microorganisms, comprising: applying to the plants, to parts thereof or the locus thereof a fungicidally effective amount of a compound of Formula (IA) or a compound of Formula (IB), or a composition comprising the compound of Formula (IA) or the compound of Formula (IB) as an active ingredient; wherein the compound of formula (IA) is:

wherein A¹ represents N or CR¹ wherein R¹ is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; A² represents N or CR², wherein R² is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; R³ and R⁴ independently represent hydrogen or halogen; wherein when A¹ is CR¹ and A² is CR², 0 to 3 of R¹ to R⁴ are hydrogen; n=0 or 1; R⁵ and R⁶ independently represent hydrogen or methyl; R⁷ represents hydrogen, C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄ha1oalkyl, C₃-₆haloalkenyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, C₁-₄haloalkoxyC₁-₆alkyl, C₁-₄alkylcarbonylC₁-₄alkyl, C₁-₄alkoxycarbonylC₁-₄alkyl, C₁-₄alkylaminocarbonylC₁-₄alkyl, di-C₁-₄alkylaminocarbonylC₁-₄alkyl, C₃-₈cycloalkyl, C₃-₈cycloalkylC₁-₃alkyl, phenyl, phenylC₁-₃alkyl, heteroaryl, heteroarylC₁-₃alkyl, wherein the heteroaryl moiety of said heteroaryl and heteroarylC₁-₃alkyl is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC₁-₃alkyl or heterocyclyloxyC₁-3alkyl, wherein the heterocyclyl moiety of said heterocyclyl, heterocyclylC₁-₃alkyl and heterocyclyloxyC₁-₃alkyl is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein any of cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2, 3 or 4 substituents, which may be the same or different, selected from R⁹; R⁸ represents hydrogen, C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄ha1oalkyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, phenyl or phenylC₁-₃alkyl; R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C₁-₄alkoxycarbonyl, C₁-₄alkylaminocarbonyl, di-C₁-₄alkylaminocarbonyl, or cyclopropyl; or R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N and NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl; or a salt or an N-oxide thereof; and wherein the compound of Formula (TB) is

wherein A¹ is CR¹, wherein R¹ is hydrogen; A² is CR², wherein R² is hydrogen; R³ and R⁴ both represent hydrogen; n=0 or 1; R⁵ and R⁶ independently represent hydrogen or methyl; R⁷ represents hydrogen, C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄ha1oalkyl, C₃-₆haloalkenyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, C₁-₄haloalkoxyC₁-₆alkyl, C₁-₄alkylcarbonylC₁-₄alkyl, C₁-₄alkoxycarbonylC₁-₄alkyl, C₁-₄alkylaminocarbonylC₁-₄alkyl, di-C₁-₄alkylaminocarbonylC₁-₄alkyl, C₃-₈cycloalkyl, C₃-₈cycloalkylC₁-₃alkyl, phenyl, phenylC₁-₃alkyl, heteroaryl, heteroarylC₁-₃alkyl, wherein the heteroaryl moiety of said heteroaryl and heteroarylC₁-₃alkyl is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC₁-₃alkyl or heterocyclyloxyC₁-₃alkyl, wherein the heterocyclyl moiety of said heterocyclyl, heterocyclylC₁-₃alkyl and heterocyclyloxyC₁-₃alkyl is a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein any of said cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2, 3 or 4 substituents, which may be the same or different, selected from R⁹; R⁸ represents hydrogen, C₁-₆alkyl, C₃-₆alkenyl, C₃-₆alkynyl, C₁-₄haloalkyl, cyanoC₁-₆alkyl, hydroxyC₁-₆alkyl, C₁-₄alkoxyC₁-₆alkyl, phenyl, or phenylC₁-₃alkyl; R⁹ represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C₁-₄alkoxycarbonyl, C₁-₄alkylaminocarbonyl, di-C₁-₄alkylaminocarbonyl, or cyclopropyl; or R⁷ and R⁸, together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N and NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR¹⁰, wherein R¹⁰ is H or C₁-₄alkyl; or a salt or an N-oxide thereof; with the proviso that the compound of Formula (IB) is not: N-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; N-methoxy-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; N-benzyloxy-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; or N-methoxy-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide. 